The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application

This review is dedicated to Emeritus Professor Metin Balci (Ataturk University and Middle East Technical University) on behalf of all Balci students, past and present, with warmest congratulations, respect, and admiration, on the occasion of his 69^th birthday.

Abstract

Numerous studies on dibenzosuberenones, especially on 5-dibenzosuberenones, have emerged in recent years. This review focuses on the chemistry of dibenzosuberenones, including their synthesis and applications, which are currently used as tools by the synthetic and biological communities.

1 Introduction

2 5-Dibenzosuberenone (5H-Dibenzo[a,d]cyclohepten-5-one)

2.1 Synthesis of 5-Dibenzosuberenone

2.2 Reactions of 5-Dibenzosuberenone

3 5H-Dibenzo[a,c]cyclohepten-5-one

3.1 Synthesis of 5H-Dibenzo[a,c]cyclohepten-5-one

3.2 Reactions of 5H-Dibenzo[a,c]cyclohepten-5-one

4 6H-Dibenzo[a,c]cyclohepten-6-one and 10H-Dibenzo[a,d]cyclohepten-10-one

4.1 Generation and Trapping of 6H-Dibenzo[a,c]cyclohepten-6-one and 10H-Dibenzo[a,d]cyclohepten-10-one

5 Dibenzocycloheptenediones

5.1 Synthesis of Dibenzocycloheptenediones

5.2 Reactions of Dibenzocycloheptenediones

6 Conclusion

Key words

dibenzosuberenone - dibenzotropone - dibenzocycloheptenediones - dibenzocycloheptene - dibenzo[7]annulene

• References

• 1 Kurihara T. Ishikawa S. Nozeo T. Aihara J.-I. Bull. Chem. Soc. Jpn. 1990; 63: 2531
• 2 Shimanouchi H. Hata T. Sasada Y. Tetrahedron Lett. 1968; 9: 3573
• 3 Oddon Y. Darbon N. Reboul JP. Cristau B. Soyfer JC. Pepe G. Acta Crystallogr., Sect. C 1984; 40: 524
• 4 Weiler-Feilchenfeld H. Solomonovic A. J. Chem Soc. B 1971; 869
• 5 Grauer Z. Yariv S. Heller-Kallai L. Avnir D. J. Therm. Anal. Calorim. 1983; 26: 49
• 6 Grauer Z. Daniel H. Avnir D. J. Colloid Interface Sci. 1983; 96: 414
• 7 Grauer Z. Peled H. Avnir D. Yariv S. Heller-Kallai L. J. Colloid Interface Sci. 1986; 111: 261
• 8 Chakraborty A. Fulara J. Maier JP. J. Chem. Phys. 2015; 143: 84312
• 9 Stewart R. Granger MR. Moodie RB. Muenster LJ. Can. J. Chem. 1963; 41: 1065
• 10 Saleh NA. Zwiefak A. Mordarski M. Pulverer G. Zentralbl. Bakteriol., Mikrobiol. Hyg., Ser. A 1988; 270: 160
• 11 Murray MA. Babe LM. Antiviral Res. 1999; 44: 123
• 12 Rajendiran N. Sankaranarayanan RK. Venkatesh G. Bull. Chem. Soc. Jpn. 2014; 87: 797
• 13 Goetz H. Heilbronner E. Katritzky AR. Jones RA. Helv. Chim. Acta 1961; 44: 387
• 14 Rabinovitz M. Agranat I. Bergmann ED. Tetrahedron 1966; 22: 225
• 15 Arnett EM. Quirk RP. Larsen JW. J. Am. Chem. Soc. 1970; 92: 3977
• 16 Diakur J. Nakashima TT. Vederas JC. Can. J. Chem. 1980; 58: 1311
• 17 Drake JA. G. Jones DW. Spectrochim. Acta, Part A 1981; 37: 77
• 18 Jin P. Wildman TA. J. Phys. Chem. 1991; 95: 20
• 19 Allan M. Heilbronner E. Kloster-Jensen E. J. Electron ­Spectrosc. Relat. Phenom. 1975; 6: 181
• 20 Gusten H. Klasinc L. Toth T. Knop JV. J. Electron Spectrosc. Relat. Phenom. 1976; 8: 417
• 21 Luisa M. Franco TM. B. Celina M. Lazana RL. R. Herold BJ. J. Chem. Soc., Perkin Trans. 2 1990; 513
• 22 Sakai M. Mizuno M. Takahashi H. J. Raman Spectrosc. 1998; 29: 919
• 23 Hrdlovic P. Srnkova K. Eur. Polym. J. 1992; 28: 1279
• 24 Cody RB. Anal. Chem. 1988; 60: 917
• 25 Nyadong L. Galhena AS. Fernandez FM. Anal. Chem. 2009; 81: 7788
• 26 Diaz A. Parra M. Banuelos R. Contreras R. J. Org. Chem. 1978; 43: 4461
• 27 Papadopoulos K. Triantis T. Tsagaraki K. Dimotikali D. Iftimie N. Meghea A. J. Photochem. Photobiol., A 2002; 152: 11
• 28 Nakai H. Baba T. J. Mol. Struct. 2005; 735–736: 211
• 29 Goez M. Sartorius I. J. Am. Chem. Soc. 1993; 115: 11123
• 30 Kavlakoglu E. Yaman A. Bayrakçeken F. Anal. Sci. 1999; 1510: 1001
• 31 Kavlakoglu E. Yaman A. Bayrakçeken F. Spectrochim. Acta, Part A 2000; 56: 1117
• 32 Bume DD. Pitts CR. Jokhai RT. Lectka T. Tetrahedron 2016; 72: 6031
• 33 Cope AC. Fenton SW. J. Am. Chem. Soc. 1951; 73: 1673
• 34 Ramesha AR. Roy AK. Synth. Commun. 2001; 31: 2419
• 35 Treibs W. Klinkhammer HJ. Chem. Ber. 1951; 84: 671
• 36 Campbell TW. Ginsig R. Schmid H. Helv. Chim. Acta 1953; 36: 1489
• 37 Sarussi L. Blum J. Avnir D. J. Sol-Gel Sci. Technol. 2000; 19: 17
• 38 Amiel Y. Ginsburg D. Tetrahedron 1957; 1: 19
• 39 Kendall JT. J. Labelled Compd. Radiopharm. 1999; 42: 477
• 40 Yanada K. Yanada R. Meguri H. J. Chem. Soc., Chem. Commun. 1990; 730
• 41 Gannon T. Mcgimpsey WG. J. Org. Chem. 1993; 58: 913
• 42 Takaguchi Y. Hosokawa A. Yamada S. Motoyoshiya J. Aoyama H. J. Chem. Soc., Perkin Trans. 1 1998; 3147
• 43 Liu X. Verkade JG. J. Org. Chem. 1999; 64: 4840
• 44 Linderman RJ. Binet S. Petrich SR. J. Org. Chem. 1999; 64: 8058
• 45 Yoo BW. Choi KH. Ko JJ. Nam GS. Chang KY. Choi KI. Kim JH. Bull. Korean Chem. Soc. 2001; 22: 541
• 46 Yoo BW. Choi JW. Kim JH. Bull. Korean Chem. Soc. 2008; 29: 1655
• 47 Yoo BW. Choi JW. Yang MH. Synth. Commun. 2009; 39: 1488
• 48 Yoo BW. Kim JH. Yang MH. Bull. Korean Chem. Soc. 2010; 31: 791
• 49 Yoo BW. Kim SH. Park YK. Synth. Commun. 2012; 42: 1632
• 50 Yoo BW. Lee SJ. Park YK. Choi YC. Ahn YS. Bull. Korean Chem. Soc. 2013; 34: 1951
• 51 Li W. Li J. Lin M. Wacharasindhu S. Tabei K. Mansour TS. J. Org. Chem. 2007; 72: 6016
• 52 McTiernan CD. Pitre SP. Scaiano JC. ACS Catal. 2014; 4: 4034
• 53 Mukhopadhyay C. Becker FF. Banik BK. J. Chem. Res. 2001; 28
• 54 Alagiri K. Prabhu KR. Tetrahedron 2011; 67: 8544
• 55 Wu J. Liu Y. Ma X. Liu P. Gu C. Dai B. Synth. Commun. 2016; 46: 1747
• 56 Nguyen TV. Hall M. Tetrahedron Lett. 2014; 55: 6895
• 57 Linares ML. Sanchez N. Alajarin R. Vaquero JJ. Alvarez-Builla J. Synthesis 2001; 382
• 58 Slates HL. Wendler NL. J. Med. Chem. 1965; 8: 886
• 59 Burbiel JC. ARKIVOC 2006; (xiii): 16; http://www.arkat-usa.org/home
• 60 Reetz MT. Eibach F. Angew. Chem., Int. Ed. Engl. 1978; 17: 278
• 61 Wan P. Budac D. Krogh E. J. Chem. Soc., Chem. Commun. 1990; 255
• 62 Mahesh M. Murphy JA. Wessle HP. J. Org. Chem. 2005; 70: 4118
• 63 Jereb M. Vražič D. Org. Biomol. Chem. 2013; 11: 1978
• 64 Stavarache C. Pocsan A.-M. Vinatoru M. Mason TJ. ­Ultrason. Sonochem. 2003; 10: 49
• 65 Epling GA. Sibley MT. Chou TT. Kumar A. Photochem. Photobiol. 1988; 47: 491
• 66 Taljaard B. Goosen A. McCleland CW. J. Chem. Soc., Perkin Trans. 1 1989; 931
• 67 Kawamura Y. Oda T. Iwano Y. Tsukayama M. Horie T. ­Phosphorus, Sulfur Silicon Relat. Elem. 1992; 73: 121
• 68 Simion A. Draghici C. Schiketanz I. Marton G. Banciu MD. J. Anal. Appl. Pyrolysis 2006; 75: 97
• 69 Pich KC. Bishop R. Craig DC. Scudder ML. J. Inclusion Phenom. Mol. Recognit. Chem. 1994; 18: 149
• 70 Rosowsky A. Papathanasopoulos N. Lazarus H. Foley GE. Modest EJ. J. Med. Chem. 1974; 17: 672
• 71 Ruecker G. Hostettmann K. Gajewski W. Loebbert M. Boeken P. Arch. Pharm. (Weinheim, Ger.) 1993; 326: 941
• 72 Coppola GM. Hardtmann GE. Koletar G. Kroin S. J. ­Heterocycl. Chem. 1981; 18: 31
• 73 Carnmalm B. Jacupovic E. Johansson L. De Paulis T. Ramsby S. Stjernström NE. Renyi AL. Ross SB. Ögren SO. J. Med. Chem. 1974; 17: 65
• 74 Looker JJ. Maier DP. Regan TH. J. Org. Chem. 1972; 37: 3401
• 75 Marxer A. Helv. Chim. Acta 1982; 65: 392
• 76 Dyker G. Hagel M. Henkel G. Köckerling M. Eur. J. Org. Chem. 2008; 3095
• 77 Li H. Zhang H.-R. Petersen JL. Wang KK. J. Org. Chem. 2001; 66: 6662
• 78 Coppola GM. Damon RE. J. Heterocycl. Chem. 1995; 32: 1133
• 79 Thomas S. Evgeni B. Tamm M. J. Chem. Soc., Perkin Trans. 2 1996; 67
• 80 Starck J.-P. Talaga P. Quere L. Collart P. Christophe B. Brutto LB. Jadot S. Chimmanamada D. Zanda M. Wagner A. Mioskowski C. Massingham R. Guyaux M. Bioorg. Med. Chem. Lett. 2006; 16: 373
• 81 Dahl BJ. Mills NS. J. Am. Chem. Soc. 2008; 130: 10179
• 82 Banide EV. Müller-Bunz H. Manning AR. Evans P. McGlinchey M. Angew. Chem. Int. Ed. 2007; 46: 2907
• 83 Brusey SA. Banide EV. Dorrich S. O’Donohue P. Ortin Y. Müller-Bunz H. Long C. Evans P. McGlinchey MJ. ­Organometallics 2009; 28: 6308
• 84 Irurre J. Farrerons C. Castañer J. Riera J. Juliá L. Tetrahedron Lett. 1992; 33: 5575
• 85 Hellwinkel D. Becker T. Chem. Ber. 1989; 122: 1595
• 86 Ogo N. Ishikawa Y. Sawada J.-I. Matsuno K. Hashimoto A. Asai A. ACS Med. Chem. Lett. 2015; 6: 1004
• 87 Weber E. Doerpinghaus N. Csoeregh I. J. Chem. Soc., Perkin Trans. 2 1990; 2167
• 88 Weber E. Wierig A. Skobridis K. J. Prakt. Chem./Chem. Ztg. 1996; 338: 553
• 89 Weber E. Nitsche S. Wierig A. Csoregh I. Eur. J. Org. Chem. 2002; 856
• 90 Jacobs A. Tangouna Liambo Bissa ML. Taljaard JH. J. Chem. Crystallogr. 2015; 45: 330
• 91 Hatano M. Ito O. Suzuki S. Ishihara K. Chem. Commun. 2010; 46: 2674
• 92 Sumita A. Gasonoo M. Boblak KJ. Ohwada T. Klumpp D. Chem. Eur. J. 2017; 23: 2566
• 93 Chang M.-Y. Huang Y.-P. J. Chin. Chem. Soc. 2013; 60: 632
• 94 Yeh C.-H. Korivi RP. Cheng C.-H. Adv. Synth. Catal. 2013; 355: 1338
• 95 Li X. Chen J. Wang D. Han F. Yao C. Acta Crystallogr., Sect. E 2007; 63: o4460
• 96 Adams TC. Dupont AC. Carter JP. Kachur JF. Guzewska ME. Rzeszotarski WJ. Farmer SG. Noronha-Blob L. Kaiser C. J. Med. Chem. 1991; 34: 1585
• 97 Sisak A. J. Organomet. Chem. 1999; 586: 48
• 98 Lever OW. Jr. Werblood HM. Russell RK. Tetrahedron Lett. 1993; 34: 203
• 99 Wiedemann SH. Bio MM. Brown LM. Hansen KB. Langille NF. Synlett 2012; 23: 2231
• 100 Akita M. Mohri S.-Y. Takahashi M. Kobayashi K. Heterocycles 2013; 87: 1319
• 101 Nordvall G. Sundquist S. Nilvebrant L. Hacksell U. Bioorg. Med. Chem. Lett. 1994; 4: 2837
• 102 Kise N. Hamada Y. Sakurai T. J. Org. Chem. 2016; 81: 5101
• 103 Kise N. Hamada Y. Sakurai T. J. Org. Chem. 2016; 81: 11043
• 104 Kise N. Hamada Y. Sakurai T. Tetrahedron 2017; 73: 1143
• 105 Garratt PJ. Knapp KA. Chem. Commun. 1971; 1084
• 106 Halton B. Buckland SJ. Mei Q. Stang PJ. Tetrahedron Lett. 1986; 27: 5159
• 107 Halton B. Buckland SJ. Lu Q. Mei Q. Stang PJ. J. Org. Chem. 1988; 53: 2418
• 108 Akiba K. Ishikawa K. Inamoto N. Synthesis 1977; 861
• 109 Akiba K. Ishikawa K. Inamoto N. Bull. Chem. Soc. Jpn. 1978; 51: 2674
• 110 Gompper R. Reiser W. Tetrahedron Lett. 1976; 17: 1263
• 111 Sugihara Y. Fujiyama Y. Murata I. Chem. Lett. 1980; 1427
• 112 Iyoda M. Tanake S. Nishioka K. Oda M. Tetrahedron Lett. 1983; 24: 2861
• 113 Luisa M. Franco ML. T. M. B. J. Lazana MC. R. L. R. J. Chem. Soc., Faraday Trans. 1994; 90: 3273
• 114 Lazana MC. R. L. R. Franco ML. T. M. B. J. Chem. Soc., Faraday Trans. 1995; 91: 3821
• 115 Andronico LA. Quintavalla A. Lombardo M. Mirasoli M. Guardigli M. Trombini C. Roda A. Chem. Eur. J. 2016; 22: 18156
• 116 Harie G. Samat A. Guglielmetti R. Mol. Cryst. Liq. Cryst. 1997; 297: 263
• 117 Cadierno V. Francos J. Gimeno J. Tetrahedron Lett. 2009; 50: 4773
• 118 Garcia-Álvarez J. Diez J. Vidal C. Vicent C. Inorg. Chem. 2013; 52: 6533
• 119 Antinolo A. Carrillo-Hermosilla F. Cadierno V. Garcia-Álvarez J. Otero A. ChemCatChem 2012; 4: 123
• 120 Wallace MA. Dean DC. Melillo DG. J. Labelled Compd. Radiopharm. 2009; 52: 514
• 121 Yoshifuji M. Takahashi H. Shimura K. Toyota K. Hirotsu K. Okada K. Heteroat. Chem. 1997; 8: 375
• 122 Rawe BW. Chun CP. Gates DP. Chem. Sci. 2014; 5: 4928
• 123 Ting PC. Lee JF. Solomon DM. Smith SR. Terminelli CA. Jakway JP. Zambas DN. Bioorg. Med. Chem. Lett. 1995; 5: 2749
• 124 Miodownik A. Kreisberger J. Nussim M. Avnir D. Synth. Commun. 1981; 11: 241
• 125 Wolf C. Shunack W. Arch. Pharm. (Weinheim, Ger.) 1996; 329: 87
• 126 Engelhardt EL. Zell HC. Saari WS. Christy ME. C. Colton D. Stone CA. Stavorski JM. Wenger HC. Ludden CT. J. Med. Chem. 1965; 8: 829
• 127 Hatano M. Ito O. Suzuki S. Ishihara K. J. Org. Chem. 2010; 75: 5008
• 128 Xu G. Kannan A. Hartman TL. Wargo H. Watson K. Turpin JA. Buckheit RW. Johnson AA. Pommier Y. Cushman M. Bioorg. Med. Chem. 2002; 10: 2807
• 129 Santroch G. Humber LG. J. Heterocycl. Chem. 1976; 13: 1049
• 130 Rokach J. Girard Y. Atkinson JG. J. Chem. Soc., Chem. Commun. 1979; 892
• 131 Szmant HH. Alciaturi CE. J. Org. Chem. 1977; 42: 1081
• 132 Brenner DG. Cavolowsky KM. Shepard KL. J. Heterocycl. Chem. 1985; 22: 805
• 133 Hjelmencrantz A. Friberg A. Berg U. J. Chem. Soc., Perkin Trans. 2. 2000; 1293
• 134 Mlostoń G. Warkentin J. Linden A. Heimgartner H. Helv. Chim. Acta 2007; 90: 2024
• 135 Kornicka A. Hudson AL. Bednarski PJ. Acta Pol. Pharm. 2009; 66: 523
• 136 Banciu MD. Simion A. Draghici C. Mihaiescu D. Oprean I. J. Anal. Appl. Pyrolysis 2000; 53: 161
• 137 Cioroianu DM. Moruşciag L. Căproiu MT. Limban C. Chiriţă IC. Nuţă DC. Farmacia (Bucharest, Rom.) 2013; 61: 469
• 138 Ciganek E. Uyeda RT. Cohen M. Smith DH. J. Med. Chem. 1981; 24: 336
• 139 Kumar M. Singh K. Naran K. Hamzabegovic F. Hoft DF. Warner DF. Ruminski P. Abate G. Chibale K. ACS Infect. Dis. 2016; 2: 714
• 140 Greb L. Lehn J.-M. J. Am. Chem. Soc. 2014; 136: 13114
• 141 Agranat I. Cohen S. Isaksson R. Sandstroem J. Suissa MR. J. Org. Chem. 1990; 55: 4943
• 142 Koumura N. Geertsema EM. Van Gelder MB. Meetsma A. Feringa BL. J. Am. Chem. Soc. 2002; 124: 5037
• 143 Safarzadeh-Amiri A. Verrall RE. Steer RP. Can. J. Chem. 1983; 61: 894
• 144 Luo J. Song K. Gu FL. Miao Q. Chem. Sci. 2011; 2: 2029
• 145 Hamera-Fałdyga R. Grzelak P. Pipiak P. Mlostoń G. ­Phosphorus, Sulfur Silicon Relat. Elem. 2017; 192: 197
• 146 Levy A. Cohen S. Pogodin S. Agranat I. Struct. Chem. 2015; 26: 1565
• 147 Zheng R.-H. Acta Crystallogr., Sect. E 2008; 64: o589
• 148 Wang Z. Shao H. Ye J. Tang L. Lu P. J. Phys. Chem. B 2005; 109: 19627
• 149 Shao H. Chen X. Wang Z. Lu P. J. Phys. Chem. B 2007; 111: 10386
• 150 Banide EV. O’Connor C. Fortune N. Ortin Y. Milosevic S. Mueller-Bunz H. McGlinchey MJ. Org. Biomol. Chem. 2010; 8: 3997
• 151 Mills NS. Cheng FE. Baylan JM. Tirla C. Hartmann JL. Patel KC. Dahl BJ. Mcclintock SP. J. Org. Chem. 2011; 76: 645
• 152 Tresca B. Higbee M.-D. Mills NS. J. Org. Chem. 2011; 76: 5539
• 153 Moriarty RM. Khosrowshahi JS. Tetrahedron Lett. 1986; 27: 2809
• 154 Zengin M. Genc H. Demirci T. Arslan M. Kucukislamoglu M. Tetrahedron Lett. 2011; 52: 2333
• 155 Cresswell AJ. Eey ST.-C. Denmark SE. Nat. Chem. 2015; 7: 146
• 156 Stavber S. Sotler-Pecan T. Zupan M. Bull. Chem. Soc. Jpn. 1996; 69: 169
• 157 Krishnan S. Kuhn DG. Hamilton GA. J. Am. Chem. Soc. 1977; 99: 8121
• 158 Chang M.-Y. Tsai C.-Y. Chan C.-K. Tetrahedron 2015; 71: 424
• 159 Fantauzzi S. Gallo E. Caselli A. Piangiolino C. Ragaini F. Cenini S. Eur. J. Org. Chem. 2007; 6053
• 160 Zbaida S. Kariv R. Biopharm. Drug Dispos. 1990; 11: 39
• 161 Rupard JH. De Paulis T. Janowsky A. Smith HE. J. Med. Chem. 1989; 32: 2261
• 162 Kopecky J. Shields JE. Tetrahedron Lett. 1968; 9: 2821
• 163 Rokach J. Girard Y. Atkinson JG. J. Chem. Soc., Chem. Commun. 1975; 602
• 164 Okamoto M. Fujiwara Y. Oka T. Uemura Y. Chem. Pharm. Bull. 1988; 36: 521
• 165 Fujiwara Y. Sumino M. Nozaki A. Okamoto M. Chem. Pharm. Bull. 1989; 37: 1452
• 166 Fujita M. Oguro D. Miyazawa M. Oka H. Yamaguchi K. Ogura K. Nature (London) 1995; 378: 469
• 167 Yoshizawa M. Takeyama Y. Okano T. Fujita M. J. Am. Chem. Soc. 2003; 125: 3243
• 168 Lozama A. Cunningham CW. Caspers MJ. Douglas JT. Dersch CM. Rothman RB. Prisinzano TE. J. Nat. Prod. 2011; 74: 718
• 169 Valdes LJ. III. Butler WM. Hatfield GM. Paul AG. Koreeda M. J. Org. Chem. 1984; 49: 4716
• 170 Ortega A. Blount JF. Manchand PS. J. Chem. Soc., Perkin Trans. 1 1982; 2505
• 171 Siebert DJ. J. Ethnopharmacol. 1994; 43: 53
• 172 Roth BL. Baner K. Westkaemper R. Siebert D. Rice KC. Steinberg S. Ernsberger P. Rothman RB. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 11934
• 173 Hicks LD. Han JK. Fry AJ. Tetrahedron Lett. 2000; 41: 7817
• 174 Liu G.-B. Zhao H.-Y. Zhu J.-D. He H.-J. Yang H.-J. Thiemann T. Tashiro H. Tashiro M. Synth. Commun. 2008; 38: 1651
• 175 Horning DE. Muchowski JM. Can. J. Chem. 1968; 46: 3665
• 176 Platzek J. Snatzke G. Tetrahedron 1987; 43: 4947
• 177 Renaud RN. Layton RB. Fraser RR. Can. J. Chem. 1973; 51: 3380
• 178 Schmuck C. Wienand W. Synthesis 2002; 655
• 179 Nakano T. Kinjo N. Hidaka Y. Okamoto Y. Polym. J. 1999; 31: 464
• 180 Childs RF. Brown MA. Anet FA. L. Winstein S. J. Am. Chem. Soc. 1972; 94: 2175
• 181 Coyne WE. Cusic JW. J. Med. Chem. 1974; 17: 72
• 182 Taljaard B. Taljaard JH. Imrie C. Caira MR. Eur. J. Org. Chem. 2005; 2607
• 183 Barnett CJ. Huff B. Kobierski ME. Letourneau M. Wilson TM. J. Org. Chem. 2004; 69: 7653
• 184 Dantzig AH. Law KL. Cao J. Starling JJ. Curr. Med. Chem. 2001; 8: 39
• 185 Moger M. Satam V. Govindaraju DR. C. Paniraj AS. Gopinath VS. Hindupur RM. Pati HN. J. Braz. Chem. Soc. 2014; 25: 104
• 186 Moger M. Pradhan A. Singh A. Govindaraju DR. C. Hindupur RM. Pati HN. Med. Chem. Res. 2016; 25: 449
• 187 Rokach J. Girard Y. Atkinson JG. Rooney CS. J. Heterocycl. Chem. 1979; 16: 205
• 188 Barcza S. Coppola GM. Hardtmann GE. Mansukhani RI. J. Org. Chem. 1975; 40: 2982
• 189 Ellison G. Brain Res. Rev. 1995; 20: 250
• 190 Lamanec TR. Bender DR. Demarco AM. Karady S. Reamer RA. Weinstock LM. J. Org. Chem. 1988; 53: 1768
• 191 Pich KC. Bishop R. Craig DC. Scudder ML. Aust. J. Chem. 1994; 47: 837
• 192 Chang M.-Y. Huang Y.-P. Lee T.-W. Chen Y.-L. Tetrahedron 2012; 68: 3283
• 193 Larsen RD. Davis P. Corley EG. Reider PJ. Lamanec TR. Grabowski EJ. J. J. Org. Chem. 1990; 55: 299
• 194 Thompson WJ. Anderson PS. Britcher SF. Lyle TA. Thies JE. Magill CA. Varga SL. Schwering JE. Lyle PA. Christy ME. Evans BE. Colton CD. Holloway MK. Springer JP. Hirshfield JM. Ball RG. Amato JS. Larsen RD. Wong EH. F. Kemp JA. Tricklebank MD. Singh L. Oles R. Priestly T. Marshall GR. Knight AR. Middlemiss DN. Woodruff GN. Iversen LL. J. Med. Chem. 1990; 33: 789
• 195 Remy DC. Anderson PS. Christy ME. Evans BE. J. Org. Chem. 1978; 43: 4311
• 196 Christy ME. Anderson PS. Britcher SF. Colton CD. Evans BE. Remy DC. Engelhardt EL. J. Org. Chem. 1979; 44: 3117
• 197 Evans BE. Anderson PS. Christy ME. Colton CD. Remy DC. Rittle KE. Engelhardt EL. J. Org. Chem. 1979; 44: 3127
• 198 Hoffmann D. Reinke H. Oehme H. J. Organomet. Chem. 1996; 526: 185
• 199 Geier J. Frison G. Grützmacher H. Angew. Chem. Int. Ed. 2003; 42: 3955
• 200 Liedtke J. Loss S. Alcaraz G. Gramlich V. Grützmacher H. Angew. Chem. Int. Ed. 1999; 38: 1623
• 201 Liedtke J. Loss S. Widauer C. Grützmacher H. Tetrahedron 1999; 56: 143
• 202 Jansen H. Lang FB. Slootweg JC. Ehlers AW. Lutz M. Lammertsma K. Gruetzmacher H. Angew. Chem. Int. Ed. 2010; 49: 5485
• 203 Lang FB. Grützmacher H. Chimia 2003; 57: 187
• 204 Chen C.-T. Wei Y. Lin J.-S. Moturu MV. R. K. Chao W.-S. Tao Y.-T. Chien C.-H. J. Am. Chem. Soc. 2006; 128: 10992
• 205 Jou JH. Su YT. Hsiao MT. Yu HH. He ZK. Fu SC. Chiang CH. Chen CT. Chou CH. Shyue JJ. J. Phys. Chem. C 2016; 120: 18794
• 206 Pillekamp M. Alachraf W. Oppel IM. Dyker G. J. Org. Chem. 2009; 74: 8355
• 207 Chung J.-Y. Schulz C. Bauer H. Sun Y. Sitzmann H. Auerbach H. Pierik AJ. Schuenemann V. Neuba A. Thiel WR. Organometallics 2015; 34: 5374
• 208 Banciu MD. Popescu A. Simion A. Draghici C. Mangra C. Mihaiescu D. Pocol M. J. Anal. Appl. Pyrolysis 1999; 48: 129
• 209 Chaffins S. Brettreich M. Wudl F. Synthesis 2002; 1191
• 210 Brusey SA. Shen W. Müller-Bunz H. Ortin Y. Evans P. McGlinchey MJ. Eur. J. Inorg. Chem. 2017; 2048
• 211 Kornmayer SC. Rominger F. Gleiter R. Synthesis 2009; 2547
• 212 Mbua NE. Guo J. Wolfert MA. Steet R. Boons G.-J. ­ChemBioChem 2011; 1912
• 213 Kii I. Shiraishi A. Hiramatsu T. Matsushita T. Uekusa H. Yoshida S. Yamamoto M. Kudo A. Hagiwara M. Hosoya T. Org. Biomol. Chem. 2010; 8: 4051
• 214 Wang L. Dai C. Chen W. Wang SL. Wang B. Chem. Commun. 2011; 47: 10377
• 215 Tanaka K. Nakamoto Y. Siwu ER. Pradipta AR. Morimoto K. Fujiwara T. Yoshidad S. Hosoyad T. Tamura Y. Hirai G. Sodeoka M. Fukase K. Org. Biomol. Chem. 2013; 11: 7326
• 216 Sun P. Chen J. Liu JA. Zhang K. Macromolecules 2017; 50: 1463
• 217 Kuzmin A. Poloukhtine A. Wolfert MA. Popik VV. ­Bioconjugate Chem. 2010; 21: 2076
• 218 Chadwick RC. Van Gyzen S. Liogier S. Adronov A. Synthesis 2014; 46: 669
• 219 Chen Q. Chu T. Bioorg. Med. Chem. Lett. 2016; 26: 5472
• 220 Cheng Z. Elias DR. Kamat NP. Johnston ED. Poloukhtine A. Popik V. Hammer DA. Tsourkas A. Bioconjugate Chem. 2011; 22: 2021
• 221 Sachin K. Jadhav VH. Kim E.-M. Kim HL. Lee SB. Jeong H.-J. Lim ST. Sohn M.-H. Kim DW. Bioconjugate Chem. 2012; 23: 1680
• 222 Campbell-Verduyn LS. Mirfeizi L. Schoonen AK. Dierckx RA. Elsinga PH. Feringa BL. Angew. Chem. Int. Ed. 2011; 50: 11117
• 223 Carpenter RD. Hausner SH. Sutcliffe JL. ACS Med. Chem. Lett. 2011; 2: 885
• 224 Liu C. Li T. Rosi NL. J. Am. Chem. Soc. 2012; 134: 18886
• 225 Cruchter T. Harms K. Meggers E. Chem. Eur. J. 2013; 19: 16682
• 226 Dai C. Draganov AB. Wang B. Heterocycl. Commun. 2010; 16: 245
• 227 Pomerantz M. Combs GL. Jr. Fink R. J. Org. Chem. 1980; 45: 143
• 228 Banciu MD. Mangra C. Petride A. Banciu A. Popilian R. Bull. Soc. Chim. Belg. 1996; 105: 329
• 229 Hegab MI. El-Gazzar AB. A. Farag IS. Gad FA. Sulfur Lett. 2002; 25: 79
• 230 Zhu X.-Q. Chen X. Mei L.-R. Org. Lett. 2011; 13: 2456
• 231 Looker JJ. A. J. Org. Chem. 1967; 32: 472
• 232 Pauson PL. Proctor GR. Watson R. J. Chem. Soc. C 1971; 2399
• 233 Ceccon A. Gambaro A. Venzo A. J. Organomet. Chem. 1984; 275: 209
• 234 Garcia MH. Valente A. Florindo P. Morais TS. Piedade MF. M. Duarte MT. Moreno V. Aviles FX. Loreno J. Inorg. Chim. Acta 2010; 363: 3765
• 235 Boucher DL. Brown MA. Mcgarvey BR. Tuck DG. J. Chem. Soc., Dalton Trans. 1999; 3445
• 236 Shang R. Ilies L. Nakamura E. J. Am. Chem. Soc. 2016; 138: 10132
• 237 Lee PY. Liang P. Yu WY. Org. Lett. 2017; 19: 2082
• 238 Sitnikov NS. Fedorov AYu. Russ. Chem. Rev. 2013; 82: 393
• 239 Seganish WM. DeShong P. Org. Lett. 2006; 8: 3951
• 240 Cook JW. Dickson GT. Loudon JD. J. Chem. Soc. 1947; 746
• 241 Buchanan GL. Cook JW. Loudon JD. Macmillan J. Nature (London) 1948; 162: 692
• 242 Pomerantz M. Dassanayake NL. McManus TR. Reynolds CH. J. Org. Chem. 1984; 49: 4029
• 243 Coburn TT. Jones WM. J. Am. Chem. Soc. 1974; 96: 5218
• 244 Blume G. Neumann T. Weyerstahl P. Justus Liebigs Ann. Chem. 1975; 201
• 245 Müller P. Pautex N. Helv. Chim. Acta 1988; 71: 1630
• 246 Choi YL. Yu C.-M. Kim BT. Heo J.-N. J. Org. Chem. 2009; 74: 3948
• 247 Debrouwer W. Fürstner A. Chem. Eur. J. 2017; 23: 4271
• 248 Hudson CE. Bauld NL. J. Am. Chem. Soc. 1973; 95: 3822
• 249 Bauld NL. Rim YS. J. Am. Chem. Soc. 1967; 89: 179
• 250 Eistert B. Minas H. Chem. Ber. 1964; 97: 2479
• 251 Eistert B. Minas H. Tetrahedron Lett. 1964; 1361
• 252 Ried W. Conte R. Chem. Ber. 1971; 104: 1573
• 253 Lucien HW. Taurins A. Can. J. Chem. 1952; 30: 208
• 254 Kodolins O. Lusis V. Muceniece D. Chem. Heterocycl. Compd. 2014; 50: 1270
• 255 Pira SL. Wallace TW. Graham JP. Org. Lett. 2009; 11: 1663
• 256 Mochida T. Izuoka A. Sato N. Sugawara T. Chem. Phys. Lett. 1993; 210: 389
• 257 Horiuchi S. Kumai R. Tokura Y. Adv. Mater. 2011; 23: 2098
• 258 Moritomo Y. Tokura Y. Mochida T. Sugawara T. Oohashi T. Kojima T. Istubo A. J. Chem. Phys. 1994; 101: 1813
• 259 Rigaudy J. Nedelec L. Bull. Soc. Chim. Fr. 1959; 659
• 260 Rigaudy J. Nedelec L. C. R. Hebd. Seances Acad. Sci. 1953; 237: 1096
• 261 Samineni R. Srihari P. Mehta G. Org. Lett. 2016; 18: 2832
• 262 Slusarczyk M. De Borggraeve WM. Hoornaert G. Robeyns K. Meervelt LV. Wu T. Deroose F. Linders J. Lett. Drug Des. Discovery 2009; 6: 478
• 263 Rigaudy J. Nedelec L. Bull. Soc. Chim. Fr. 1959; 638
• 264 Domnin NA. Kolinskii RC. Zh. Obsh. Khim. 1960; 30: 270
• 265 De Paulis T. Betts CR. Smith HE. Mobley PL. Manier DH. Sulser F. J. Med. Chem. 1981; 24: 1021
• 266 Leonard NJ. Kresge AJ. Oki M. J. Am. Chem. Soc. 1955; 77: 5078
• 267 Rigaudy J. Nedelec L. C. R. Hebd. Seances Acad. Sci. 1953; 236: 1287
• 268 Inoue H. Sakurai T. J. Chem. Soc., Chem. Commun. 1983; 314
• 269 Inoue H. Sakurai T. Hoshi T. Okubo J. Kawashima T. J. Chem. Soc., Faraday Trans. 2 1986; 82: 523
• 270 Bibaut-Renauld C. Burget D. Fouassier JP. Varelas CG. Thomatos J. Tsagaropoulos G. Ryrfors LO. Karlsson OJ. J. Polym. Sci. 2002; 40: 3171
• 271 Malval JP. Dietlin C. Allonas X. Fouassier JP. J. Photochem. Photobiol., A 2007; 192: 66
• 272 Ried W. Conte R. Chem. Ber. 1972; 105: 1224
• 273 Benati L. Montevecchi PC. Spagnolo P. Gazz. Chim. Ital. 1992; 122: 249
• 274 Namekata N. Takase K. Takahashi K. Chem. Lett. 1987; 2253
• 275 Takahashi K. Ogiyama M. Chem. Lett. 1991; 129
• 276 Konar A. Gronowitz S. Chem. Scr. 1984; 23: 5
• 277 Huang N.-Z. Lakshmikantham MV. Cava MP. J. Org. Chem. 1987; 52: 169
• 278 Katz JD. Jewell JP. Guerin DJ. Lim J. Dinsmore CJ. Deshmukh SV. Pan B. Marshall CG. Lu W. Altman MD. Dahlberg WK. Davis L. Falcone D. Gabarda AE. Hang G. Hatch H. Holmes R. Kunii K. Lumb KJ. Lutterbach B. Mathvink R. Nazef N. Patel SB. Qu X. Reilly JF. Rickert KW. Rosenstein C. Soisson SM. Spencer KB. Szewczak AA. Walker D. Wang W. Young J. Zeng Q. J. Med. Chem. 2011; 54: 4092
• 279 Wei Y. Samori S. Tojo S. Fujitsuka M. Lin JS. Chen CT. Majima T. J. Am. Chem. Soc. 2009; 131: 6698
• 280 Lombardino JC. J. Heterocycl. Chem. 1974; 11: 17
• 281 Slusarczyk M. De Borggraeve WM. Toppet S. Hoornaert GJ. Eur. J. Org. Chem. 2007; 2987
• 282 Ding Y. Girardet JL. Smith KL. Larson G. Prigaro B. Lai VC. Zhong WD. Wu JZ. Bioorg. Med. Chem. Lett. 2005; 15: 675
• 283 Geiger J. Expert Opin. Investig. Drugs 2001; 10: 865
• 284 Abrahams SL. Hazen RJ. Batson AG. Phillips AP. J. ­Pharmacol. Exp. Ther. 1989; 249: 359