RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
CC BY 4.0 · Synthesis 2017; 49(17): 3801-3834
DOI: 10.1055/s-0036-1589500
DOI: 10.1055/s-0036-1589500
review
Recent Advances in the Synthesis of Hydrogenated Azocine-Containing Molecules
This publication was supported by the Ministry of Education and Science of the Russian Federation (Agreement number 02.a03.21.0008). The financial support of the Russian Foundation for Basic Research (Grant # 17-03-00605) is gratefully acknowledged.Weitere Informationen
Publikationsverlauf
Received: 22. Januar 2017
Accepted after revision: 05. April 2017
Publikationsdatum:
01. August 2017 (online)
Dedicated to the memory of Professor N. S. Prostakov (1917–2007) on the occasion of his 100th anniversary.
Abstract
This review covers recent advances in synthesis of azocine-containing systems. The most approaches towards azocines are discussed.
1 Introduction
2 Ring-Expansion Reaction
2.1 Ring-Expansion Reaction of Cyclopentane Containing the 1,4-Diketone Moiety with Primary Amines (from 5 to 8)
2.2 Ring-Expansion Reaction of Annulated Tetrahydropyridines under the Action of Activated Alkynes (from 6 to 8)
2.3 Reductive Ring-Expansion Reaction of Cyclic Oximes
2.4 Other Ring-Expansion Reactions
3 Heck Reaction
4 Cycloaddition
5 Ring-Closing Metathesis (RCM)
6 Cyclization
6.1 Metal-Catalyzed Cyclization
6.2 Radical Cyclization
6.3 Friedel–Crafts Cyclization
6.4 Other Examples of Cyclizations
7 Microwave- and Photo-Assisted Reactions
8 Other Methods
8.1 Cascade and Tandem Reactions
8.2 Aldol Condensation
8.3 Thermolysis
8.4 Ring Opening
8.5 Other Methods
9 Conclusion
-
References
- 1 Voskressensky LG. Kulikova LN. Borisova TN. Varlamov AV. Adv. Heterocycl. Chem. 2008; 96: 81
- 2 Rössle M. Christoffers J. Synlett 2006; 106
- 3 Behler F. Habecker F. Saak W. Klüner T. Christoffers J. Eur. J. Org. Chem. 2011; 4231
- 4 Penning M. Christoffers J. Eur. J. Org. Chem. 2014; 2140
- 5 Penning M. Aeissen E. Christoffers J. Synthesis 2015; 47: 1007
- 6 Varlamov AV. Borisova TN. Voskressensky LG. Soklakova TA. Kulikova LN. Chernyshov AA. Alexandrov GG. Tetrahedron Lett. 2002; 43: 6767
- 7 Voskressensky LG. Borisova TN. Ovcharov MV. Kulikova LN. Sorokina EA. Borisov RS. Varlamov AV. Chem. Heterocycl. Compd. 2008; 44: 1510
- 8 Voskressensky LG. Borisova TN. Ovcharov MV. Sorokina EA. Khrustalev VN. Varlamov AV. Russ. Chem. Bull. 2012; 61: 1603
- 9 Voskressensky LG. Kovaleva SA. Borisova TN. Listratova AV. Eresko AB. Tolkunov VS. Tolkunov SV. Varlamov AV. Tetrahedron 2010; 66: 9421
- 10 Voskressensky LG. Ovcharov MV. Borisova TN. Kulikova LN. Listratova AV. Borisov RS. Varlamov AV. Chem. Heterocycl. Compd. 2011; 47: 222
- 11 Voskressensky LG. Ovcharov MV. Borisova TN. Listratova AV. Kulikova LN. Sorokina EA. Gromov SP. Varlamov AV. Chem. Heterocycl. Compd. 2013; 49: 1180
- 12 Voskressensky LG. Kovaleva SA. Borisova TN. Eresko AB. Tolkunov VS. Tolkunov SV. Listratova AV. Candia M. Altomare C. Varlamov AV. Chem. Heterocycl. Compd. 2013; 49: 930
- 13 Voskressensky LG. Borisova TN. Chervyakova TM. Matveeva MD. Galaktionova DV. Tolkunov SV. Tolkunova VS. Eresko AB. Varlamov AV. Chem. Heterocycl. Compd. 2014; 50: 1338
- 14 Voskressensky LG. Borisova TN. Chervyakova TM. Titov AA. Kozlov AV. Sorokina EA. Samavati R. Varlamov AV. Chem. Heterocycl. Compd. 2014; 50: 658
- 15 Voskressensky LG. Titov AA. Kobzev MS. Samavati R. Borisov RS. Kulikova LN. Varlamov AV. Chem. Heterocycl. Compd. 2016; 52: 68
- 16 Voskressensky LG. Borisova TN. Kovaleva SA. Listratova AV. Kulikova LN. Khrustalev VN. Ovcharov MV. Varlamov AV. Russ. Chem. Bull. 2012; 61: 370
- 17 Voskressensky LG. Kovaleva SA. Borisova TN. Titov AA. Toze F. Listratova AV. Khrustalev VN. Varlamov AV. Chem. Heterocycl. Compd. 2015; 51: 17
- 18a Borisov RS. Voskressensky LG. Polyakov AI. Borisova TN. Varlamov AV. Synlett 2014; 25: 0955
- 18b Zubkov FI. Ershova JD. Orlova AA. Zaytsev VP. Nikitina EV. Peregudov AS. Gurbanov AV. Borisov RS. Khrustalev VN. Maharramov AM. Varlamov AV. Tetrahedron 2009; 65: 3789
- 19 Voskressensky LG. Listratova AV. Borisova TN. Kovaleva SA. Borisov RS. Varlamov AV. Tetrahedron 2008; 64: 10443
- 20 Voskressensky LG. Kulikova LN. Gozun SV. Khrustalev VN. Borisova TN. Listratova AV. Ovcharov MV. Varlamov AV. Tetrahedron Lett. 2011; 52: 4189
- 21 Voskressensky LG. Borisov RS. Kulikova LN. Kleimenov AV. Borisova TN. Varlamov AV. Chem. Heterocycl. Compd. 2012; 48: 680
- 22 Cho H. Iwama Y. Sugimoto K. Kwon E. Tokuyama H. Heterocycles 2009; 78: 1183
- 23 Cho H. Iwama Y. Sugimoto K. Mori S. Tokuyama H. J. Org. Chem. 2010; 75: 627
- 24 Cho H. Tetrahedron 2014; 70: 3527
- 25 Cho H. Iwama Y. Okano K. Tokuyama H. Synlett 2013; 24: 813
- 26 González-Gómez Á. Domónguez G. Pérez-Castells J. Tetrahedron 2009; 65: 3378
- 27 Zhang L. Chang L. Hu H. Wang H. Yao Z.-J. Wang S. Chem. Eur. J. 2014; 20: 2925
- 28 Harthong S. Bach R. Besnard C. Guénée L. Lacour J. Synthesis 2013; 45: 2070
- 29 Mohammadizadeh MR. Alborz M. Tetrahedron Lett. 2014; 55: 6808
- 30 Malkova AV. Polyanskii KB. Soldatenkov AT. Soldatova SA. Merkulova NL. Khrustalev VN. Russ. J. Org. Chem. 2016; 52: 219
- 31 Majumdar KC. Chattopadhyay B. Samanta S. Tetrahedron Lett. 2009; 50: 3178
- 32 Majumdar KC. Samanta S. Chattopadhyay B. Tetrahedron Lett. 2009; 50: 4866
- 33 Majumdar KC. Samanta S. Chattopadhyay B. Nandi RK. Synthesis 2010; 985
- 34 Majumdar KC. Mondal S. Ghosh D. Chattopadhyay B. Synthesis 2010; 1315
- 35 Majumdar KC. Ghosh T. Chakravorty S. Tetrahedron Lett. 2010; 51: 3372
- 36 Lee HS. Kim SH. Kim TH. Kim JN. Tetrahedron Lett. 2008; 49: 1773
- 37 Lee HS. Kim SH. Gowrisankar S. Kim JN. Tetrahedron 2008; 64: 7183
- 38 Sunderhaus JD. Dockendorff C. Martin SF. Tetrahedron 2009; 65: 6454
- 39 Bennasar M.-L. Zulaica E. Solé D. Alonso S. Tetrahedron 2012; 68: 4641
- 40 Sahn JJ. Martin SF. Tetrahedron Lett. 2011; 52: 6855
- 41 Jäger M. Görls H. Günther W. Schubert US. Chem. Eur. J. 2013; 19: 2150
- 42 Peshkov AA. Peshkov VA. Pereshivko OP. Van Hecke K. Kumar R. Van der Eycken EV. J. Org. Chem. 2015; 80: 6598
- 43 Yu RT. Friedman RK. Rovis T. J. Am. Chem. Soc. 2009; 131: 13250
- 44 Koya S. Yamanoi K. Yamasaki R. Azumaya I. Masu H. Saito S. Org. Lett. 2009; 11: 5438
- 45 Kumar P. Zhang K. Louie J. Angew. Chem. Int. Ed. 2012; 51: 8602
- 46 Thakur A. Facer ME. Louie J. Angew. Chem. Int. Ed. 2013; 52: 12161
- 47 Shaw MH. Croft RA. Whittingham WG. Bower JF. J. Am. Chem. Soc. 2015; 137: 8054
- 48 Hassam M. More SV. Li W.-S. Mendeleev Commun. 2014; 24: 159
- 49 Pavlyuk O. Teller H. McMills MC. Tetrahedron Lett. 2009; 50: 2716
- 50 Wood K. Black DSt. C. Namboothiri IN. N. Kumar N. Tetrahedron Lett. 2010; 51: 1606
- 51 Wood K. Black DSt. C. Kumar N. Tetrahedron 2011; 67: 4093
- 52 Majumdar KC. Mondal S. Ghosh D. Synthesis 2010; 1176
- 53 Majumdar KC. Samanta S. Chattopadhyay B. Nandi RK. Synthesis 2010; 863
- 54 Fadeyi OO. Senter TJ. Hahn KN. Lindsley CW. Chem. Eur. J. 2012; 18: 5826
- 55 Senter TJ. Schulte ML. Konkol LC. Wadzinski TE. Lindsley CW. Tetrahedron Lett. 2013; 54: 1645
- 56 Benedetti E. Lomazzi M. Tibiletti F. Goddard J.-P. Fensterbank L. Malacria M. Palmisano G. Penoni A. Synthesis 2012; 44: 3523
- 57 Curto JM. Kozlowski MC. J. Org. Chem. 2014; 79: 5359
- 58 Dhara K. Midya GC. Dash J. J. Org. Chem. 2012; 77: 8071
- 59 Moss TA. Tetrahedron Lett. 2013; 54: 4254
- 60 Jagadeesh Y. Ramakrishna K. Rao BV. Tetrahedron: Asymmetry 2012; 23: 697
- 61 Sletten EM. Bertozzi CR. Org. Lett. 2008; 10: 3097
- 62 Mak XY. Crombie AL. Danheiser RL. J. Org. Chem. 2011; 76: 1852
- 63 Willumstad TP. Haze O. Mak XY. Lam TY. Wang Y.-P. Danheiser RL. J. Org. Chem. 2013; 78: 11450
- 64 Bennasar M.-L. Zulaica E. Solé D. Roca T. García-Díaz D. Alonso S. J. Org. Chem. 2009; 74: 8359
- 65 Bennasar M.-L. Solé D. Zulaica E. Alonso S. Tetrahedron 2013; 69: 2534
- 66 Nilson MG. Funk RL. Org. Lett. 2010; 12: 4912
- 67 Brahma K. Achari B. Chowdhury C. Synthesis 2013; 45: 545
- 68 Putey A. Popowycz F. Do Q.-T. Bernard P. Talapatra SK. Kozielski F. Galmarini CM. Joseph B. J. Med. Chem. 2009; 52: 5916
- 69 Blaszykowski C. Aktoudianakis E. Alberico D. Bressy C. Hulcoop DG. Jafarpour F. Joushaghani A. Laleu B. Lautens M. J. Org. Chem. 2008; 73: 1888
- 70 Donets PA. Van Hecke K. Van Meervelt LE. Van der Eycken V. Org. Lett. 2009; 11: 3618
- 71 Peshkov VA. Van Hove S. Donets PA. Pereshivko OP. Van Hecke K. Van Meervelt L. Van der Eycken EV. Eur. J. Org. Chem. 2011; 1837
- 72 Kumar A. Li Z. Sharma SK. Parmar VS. Van der Eycken EV. Chem. Commun. 2013; 49: 6803
- 73 Modha SG. Vachhani DD. Jacobs J. Van Meervelt L. Van der Eycken EV. Chem. Commun. 2012; 48: 6550
- 74 Alcaide B. Almendros P. Cembellín S. del Campo TM. J. Org. Chem. 2015; 80: 4650
- 75 Tokimizu Y. Oishi S. Fujii N. Ohno H. Org. Lett. 2014; 16: 3138
- 76 Ferrer C. Escribano-Cuesta A. Echavarren AM. Tetrahedron 2009; 65: 9015
- 77 Majumdar KC. Mondal S. Ghosh D. Tetrahedron Lett. 2010; 51: 348
- 78 Zhang J. Wang Y.-Q. Wang X.-W. Li W.-DZ. J. Org. Chem. 2013; 78: 6154
- 79 Diaba F. Martínez-Laporta A. Bonjoch J. J. Org. Chem. 2014; 79: 9365
- 80 Fang X. Liu K. Li C. J. Am. Chem. Soc. 2010; 132: 2274
- 81 Cincinelli R. Dallavalle S. Merlini L. Nannei R. Scaglioni L. Tetrahedron 2009; 65: 3465
- 82 Pandey G. Kant R. Batra S. Tetrahedron Lett. 2015; 56: 930
- 83 Seo S.-Y. Kim G. Tetrahedron Lett. 2015; 56: 3835
- 84 Patir S. Uludag N. Tetrahedron 2009; 65: 115
- 85 Yokosaka T. Nemoto T. Hamada Y. Chem. Commun. 2012; 48: 5431
- 86 Yokosaka T. Kanehira T. Nakayama H. Nemoto T. Hamada Y. Tetrahedron 2014; 70: 2151
- 87 Martin CL. Overman LE. Rohde JM. J. Am. Chem. Soc. 2010; 132: 4894
- 88 Falcon BV. Creighton CJ. Parker MH. Reitz AB. Synth. Commun. 2008; 38: 411
- 89 Ranatunga S. Tang C.-HA. Kang CW. Kriss CL. Kloppenburg BJ. Hu C.-CA. Del Valle JR. J. Med. Chem. 2014; 57: 4289
- 90 Alcaide B. Almendros P. Aragoncillo C. Fernandez I. Gomez-Campillos G. J. Org. Chem. 2014; 79: 7075
- 91 Bariwal JB. Ermolat’ev DS. Glasnov TN. Van Hecke K. Mehta VP. Van Meervelt L. Kappe CO. Van der Eycken EV. Org. Lett. 2010; 12: 2774
- 92 Cheung LL. W. Yudin AK. Org. Lett. 2009; 11: 1281
- 93 Cheung LL. W. Yudin AK. Chem. Eur. J. 2010; 16: 4100
- 94 Smith MR. Blake AJ. Hayes CJ. Stevens MF. G. Moody CJ. J. Org. Chem. 2009; 74: 9372
- 95 Mukhina OA. Kumar NN. B. Cowge TM. Kutateladze AG. J. Org. Chem. 2014; 79: 10956
- 96 Nakamura I. Sato Y. Takeda K. Terada M. Chem. Eur. J. 2014; 20: 10214
- 97 Zhao C. Xie X. Duan S. Li H. Fang R. She X. Angew. Chem. Int. Ed. 2014; 53: 10789
- 98 Feng S. Wang Z. Zhang W. Xie X. She X. Chem. Asian J. 2016; 11: 2167
- 99 Anand A. Singh P. Mehra V. Amandeep, Kumar V. Mahajan MP. Tetrahedron Lett. 2012; 53: 2417
- 100 Granger BA. Jewett IT. Butler JD. Martin SF. Tetrahedron 2014; 70: 4094
- 101 Huo H.-H. Zhang H.-K. Xia X.-E. Huang P.-Q. Org. Lett. 2012; 14: 4834
- 102 Huo H.-H. Xia X.-E. Zhang H.-K. Huang P.-Q. J. Org. Chem. 2013; 78: 455
- 103 Uludag N. Yılmaz R. Asutay O. Colak N. Chem. Heterocycl. Compd. 2016; 52: 196
- 104 Hehir S. O’Donovan L. Carty MP. Aldabbagh F. Tetrahedron 2008; 64: 4196
- 105 Poloukhtine A. Rassadin V. Kuzmin A. Popik VV. J. Org. Chem. 2010; 75: 5953
- 106 Prasad B. Adepu R. Sharma AK. Pal M. Chem. Commun. 2015; 51: 1259
- 107 Yavari I. Seyfi S. Synlett 2012; 23: 1209
- 108 Patil VP. Ghosh A. Sonavane U. Joshi R. Sawant R. Jadhav S. Waghmode SB. Tetrahedron: Asymmetry 2014; 25: 489
- 109 Liu R.-R. Li B.-L. Lu J. Shen C. Gao J.-R. Jia Y.-X. J. Am. Chem. Soc. 2016; 138: 5198
- 110 Xu R. Xia R. Luo M. Xu X. Cheng J. Shao X. Li Z. J. Agric. Food Chem. 2014; 62: 381
- 111 Aron ZD. Ito T. May TL. Overman LE. Wang J. J. Org. Chem. 2013; 78: 9929
- 112 Gong X. Chen M. Yao L. Wu J. Chem. Asian. J. 2016; 11: 1613
- 113 Boeckman RK. Jr. Genung NE. Chen K. Ryder TR. Org. Lett. 2010; 12: 1628
- 114 Daidone G. Sprio V. Plescia S. Marino ML. Bombieri G. Bruno G. J. Chem. Soc., Perkin Trans. 2 1989; 137
- 115 Maggio B. Raffa D. Raimondi MV. Cusimano MG. Plescia F. Cascioferro S. Cancemi G. Lauricella M. Carlisi D. Daidone G. Eur. J. Med. Chem. 2014; 72: 1
- 116 Vicente J. Saura-Llamas I. Garcıa-López J.-A. Bautista D. Organometallics 2010; 29: 4320
- 117 Frutos-Pedreno R. Gonzalez-Herrero P. Vicente J. Organometallics 2012; 31: 3361
- 118 García-Lopez J.-A. Oliva-Madrid M.-J. Saura-Llamas I. Bautista D. Vicente J. Organometallics 2012; 31: 6351
- 119 Oliva-Madrid M.-J. García-Lopez J.-A. Saura-Llamas I. Bautista D. Vicente J. Organometallics 2014; 33: 6420