Formation of Five- and Six-Membered Heterocyclic Rings under Radical Cyclization Conditions

K. C. Majumdar; Galla V. Karunakar; Biswajit Sinha

doi:10.1055/s-0032-1316566

Synthesis, Table of Contents

Synthesis 2012; 44(16): 2475-2505
DOI: 10.1055/s-0032-1316566

review

Formation of Five- and Six-Membered Heterocyclic Rings under Radical Cyclization Conditions

Authors

K. C. Majumdar*

^aDepartment of Chemical Sciences, Tezpur University, Napaam, Tezpur 784024, Assam, India

^bDepartment of Chemistry, University of Kalyani, Kalyani 741235, India, Fax: +91(33)25827521 Email: kcm@klyuniv.ac.in
Galla V. Karunakar

^aDepartment of Chemical Sciences, Tezpur University, Napaam, Tezpur 784024, Assam, India
Biswajit Sinha

^bDepartment of Chemistry, University of Kalyani, Kalyani 741235, India, Fax: +91(33)25827521 Email: kcm@klyuniv.ac.in

Abstract

All articles of this category

Abstract

This review describes the formation of five- and six-membered heterocyces in various organic molecules by radical cyclization and covers the progress made on the topic during the period of 2008 through 2010.

1 Introduction

2 Reagents, Solvents, Radical Initiators, and Reactivity

3 General Mechanistic Pathways: Regio- and Stereoselectivity

4 Synthesis of Nitrogen Heterocycles

4.1 Nitrogen-Centered Radical Cyclizations

4.2 N-Vinylic and Related Systems

4.3 N-Allylic and Related Systems

4.4 N-Alkyl and Related Systems

4.5 Diastereoselective Radical Cyclizations

4.6 Cascade and Tandem Radical Cyclizations

4.7 Atom- and Group-Transfer Radical Cyclizations

4.8 Oxidative Radical Cyclizations

4.9 Miscellaneous

5 Synthesis of Oxygen Heterocycles

5.1 Diastereoselective Radical Cyclizations

5.2 Miscellaneous

6 Synthesis of Sulfur Heterocycles

7 Synthesis of Silicon Heterocycles

8 Miscellaneous

9 Conclusions

Key words

radical cyclization - tributyltin hydride - cascade cyclization - nitrogen heterocycles - radical relay cyclization - atom-transfer radical cyclization - tandem radical cyclization - oxidative radical cyclization

Full Text

References

References
1 Present address: Crop Protection Chemicals Division, Indian Institute of Chemical Technology, Hyderabad 500607, India.

2a Eicher T, Hauptmann S. The Chemistry of Heterocycles: Structure, Reactions, Synthesis and Applications. Wiley-VCH; Weinheim: 2003

For reviews on biologically active nitrogen heterocycles, see:

2b Kang EJ, Lee E. Chem. Rev. 2005; 105: 4348
2c Saleem M, Kim HJ, Ali MS, Lee YS. Nat. Prod. Rep. 2005; 22: 696
2d Bermejo A, Figadere B, Zafra-Polo M.-C, Barrachina I, Estornell E, Cortes D. Nat. Prod. Rep. 2005; 22: 269
2e Daly JW, Spande TF, Garraffo HM. J. Nat. Prod. 2005; 68: 1556

3a Giese B. Radicals in Organic Synthesis: Formation of Carbon–Carbon Bonds. Pergamon; Oxford: 1986
3b Kim S, Joon J.-Y. Novel Radical Traps, In Radicals in Organic Synthesis . 1st ed., Vol. 2, Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001: Chap. 1
3c Curran DP. Comprehensive Organic Synthesis . Vol. 4, Trost BM, Fleming I. Pergamon Press; Oxford: 1991. Chap. 4.2, 811
3d Motherwell WB, Crich D. Best Synthetic Methods: Free Radical Chain Reactions in Organic Synthesis. Academic Press; London: 1991
3e Feray L, Kuznersov N, Renaud P In Radicals in Organic Synthesis. Vol. 2, Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001: 246
3f Curran DP, Porter NA, Giese B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications. VCH; Weinheim: 1996. Chap. 2, 23

4a Fallis AG, Brinza IM. Tetrahedron 1997; 53: 17543
4b Friestad GK. Tetrahedron 2001; 57: 5461
4c Zard SZ. Chem. Soc. Rev. 2008; 37: 1603
4d Stella L In Radicals in Organic Synthesis. Vol. 2. Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001: 407

5a Majumdar KC, Basu PK, Chattopadhyay SK. Tetrahedron 2007; 63: 793
5b Majumdar KC, Basu PK, Mukhopadhyay PP. Tetrahedron 2005; 61: 10603
5c Majumdar KC, Mukhopadhyay PP, Basu PK. Tetrahedron 2004; 60: 6239
5d Majumdar KC, Basu PK. Heterocycles 2002; 57: 2413

6 Poupaert J, Carato P, Colacino E, Yous S. Curr. Med. Chem. 2005; 12: 877
7 Majumdar KC. RSC Adv. 2011; 1152

8a Giese B, Kopping B, Gobel T, Dickhaut J, Thoma G, Kulicke KJ, Trach F. Org. React. 1996; 48: 301
8b Majumdar KC, Basu PK, Gonzalez A. Curr. Org. Chem. 2009; 13: 599
8c Rowlands GJ. Tetrahedron 2009; 65: 8603
8d Rowlands GJ. Tetrahedron 2010; 66: 1593

9a Radicals in Organic Synthesis. Vol. 1. Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001
9b For a review on n-Bu₃SnH in organic synthesis, see: Davies AG. J. Chem. Res. 2006; 141

10a Justicia J, De Cienfuegos LA, Campan AG, Miguel D, Jakoby V, Gansäuer A, Cuerva JM. Chem. Soc. Rev. 2011; 40: 3525
10b Wefelscheid UK, Berndt M, Reibig H.-U. Eur. J. Org. Chem. 2008; 3635
10c Pintauer T, Matyjaszewski K. Chem. Soc. Rev. 2008; 37: 1087

11a Perchyonok VT, Lykakis IN, Tuck KL. Green Chem. 2008; 10: 153
11b Murphy JA, Tripoli R, Khan TA, Mali UW. Org. Lett. 2005; 7: 3287
11c Hinkens DM, Midland MM. J. Org. Chem. 2009; 74: 4143
11d Kita Y, Nambu H, Ramesh NG, Anikumar G, Matsugi M. Org. Lett. 2001; 3: 1157
11e Graham AE, Thomas AV, Yang R. J. Org. Chem. 2000; 65: 2583

12a Len C, Mondon M, Lebreton J. Tetrahedron 2008; 64: 7453
12b Walker SR, Carter EJ, Huff BC, Morris JC. Chem. Rev. 2009; 109: 3080
12c Lalevée J, Tehfe M.-A, Gigmes D, Fouassier JP. Macromolecules 2010; 43: 6608
12d Sibi MP, Yang Y.-H, Lee S. Org. Lett. 2008; 10: 5349

13 Majumdar KC, Debnath P. Tetrahedron 2008; 64: 9799

14a Montevecchi PC, Navacchia ML. Tetrahedron 2000; 56: 9339
14b Mu X.-J, Zou J.-P, Zeng R.-S, Wu J.-C. Tetrahedron Lett. 2005; 46: 4345
14c Buyck LD, Danieli C, Ghelfi F, Pagnoni UM, Parsons AF, Pattarozzi M, Roncaglia F. Tetrahedron 2005; 61: 2871
14d Chen H.-L, Lin C.-Y, Cheng Y.-C, Tsai A.-I, Chuang C.-P. Synthesis 2005; 977

15a Shao J, Geacintov NE, Shafirovich V. J. Phys. Chem. B 2010; 114: 6685
15b Halpenny GM, Olmstead MM, Mascharak PK. Inorg. Chem. 2007; 46: 6601

16 Jasperse CP. Chem. Rev. 1991; 91: 1237

17a Baldwin JE, Cutting J, Dupont W, Kruse L, Silberman L, Thomas RC. J. Chem. Soc., Chem. Commun. 1976; 736
17b Baldwin JE. Further Perspectives in Organic Chemistry: A Ciba Foundation Symposium. Elsevier; Amsterdam: 1978: 85

18a Houk KN, Paddon-Row MN, Spellmeyer DC, Rondan NG, Nagase S. J. Org. Chem. 1986; 51: 2874
18b Spellmeyer DC, Houk KN. J. Org. Chem. 1987; 52: 959
18c Beckwith AL. J, Schiesser CH. Tetrahedron Lett. 1985; 26: 373
18d Beckwith AL. J, Schiesser CH. Tetrahedron 1985; 41: 3925

19 Beckwith AL. J, Easton CJ, Lawrence T, Serelis AK. Aust. J. Chem. 1983; 36: 545

20a Rajanbabu TV. J. Am. Chem. Soc. 1987; 109: 609
20b Rajanbabu TV. J. Org. Chem. 1988; 53: 4522
20c Rajanbabu TV, Fukanaga T. J. Am. Chem. Soc. 1989; 111: 296
20d Rajanbabu TV, Fukanaga T, Reddy GS. J. Am. Chem. Soc. 1989; 111: 1759

21 Cubillo FP, Scanlan EM, Scott JS, Walton JC. Chem. Commun. 2008; 4189
22 Cubillo FP, Lymer J, Scanlan EM, Scott JS, Walton JC. Tetrahedron 2008; 64: 11908
23 Beaume A, Courillon C, Derat E, Malacria M. Chem.–Eur. J. 2008; 14: 1238
24 Du Y, Xue J, Li M, Guan X, McCamant DW, Phillips DL. Chem.–Eur. J. 2010; 16: 6961
25 Xu H.-C, Brandt JD, Moeller KD. Tetrahedron Lett. 2008; 49: 3868
26 Xu H.-C, Moeller KD. J. Am. Chem. Soc. 2008; 130: 13542
27 Herzog S, Buehrdel G, Beckert R, Klimas S, Wurthwein EU, Grimme S, Gorls H. Synthesis 2009; 4049

28a Cadogan JI. G, Clark BA. J, Ford D, MacDonald RJ, MacPherson AD, McNab H, Nicolson IS, Reed D, Sommerville CC. Org. Biomol. Chem. 2009; 7: 5173
28b Crawford LA, McNab H, Mount AR, Verhille J, Wharton SI. Synthesis 2010; 923

29a Curran DP, Guthrie DB, Geib SJ. J. Am. Chem. Soc. 2008; 130: 8437
29b Bogen S, Goddard J.-P, Fensterbank F, Malacria M. ARKIVOC 2008; (viii): 126

30 Fuwa H, Sasaki M. J. Org. Chem. 2009; 74: 212
31 Taniguchi T, Yonei D, Sasaki M, Tamura O, Ishibashi H. Tetrahedron Lett. 2008; 64: 2634
32 Hernandez S, Moreno I, SanMartin R, Gomez G, Herrero MT, Dominguez E. J. Org. Chem. 2010; 75: 434

33a Pereira J, Barlier M, Guillou C. Org. Lett. 2007; 9: 3101
33b Moisan L, Wagner M, Comesse S, Doris E. Tetrahedron Lett. 2006; 47: 9093

34 Lanza T, Minozzi M, Monesi A, Nanni D, Spagnolo P, Zanardi G. Adv. Synth. Catal. 2010; 352: 2275
35 Majumdar KC, Mondal S, Ghosh D. Tetrahedron Lett. 2010; 51: 5273
36 Clyne MA, Aldabbagh F. Org. Biomol. Chem. 2006; 4: 268
37 Clive DL. J, Peng J, Fletcher SP, Ziffle VE, Wingert D. J. Org. Chem. 2008; 73: 2330

38a Coldham I, Jana S, Watson L, Martin NG. Org. Biomol. Chem. 2009; 7: 1674
38b Xu F, Simmons B, Reamer RA, Corley E, Murry J, Tschaen D. J. Org. Chem. 2008; 73: 312
38c Yadav JS, Gayathri KU, Reddy BV. S, Prasad AR. Synlett 2009; 43
38d Liermann JC, Opatz T. J. Org. Chem. 2008; 73: 4526

39 Martínez R, Menez-Arzate M, Ramírez-Apan MT. Bioorg. Med. Chem. 2009; 17: 1849
40 Gutierrez PE. R, Camacho JR, Apan MT. R, Osarnio YM, Martinez R. Org. Biomol. Chem. 2010; 8: 4374

41a Zhou W, Zhang L, Jiao N. Tetrahedron 2009; 65: 1982
41b Seitz W, Geneste H, Backfisch G, Delzer J, Graef C, Hornberger W, Kling A, Subkowski T, Zimmermann N. Bioorg. Med. Chem. Lett. 2008; 18: 527

42 Guthrie DB, Geib SJ, Curran DP. J. Am. Chem. Soc. 2009; 131: 15492

43a Kumar KS, Chaudhari VD, Dhavale DD. Org. Biomol. Chem. 2008; 6: 703
43b Pohmakotr M, Prateeptongkum S, Chooprayoon S, Tuchinda P, Reutrakul V. Tetrahedron 2008; 64: 2339

44 Lamberto M, Kilburn JD. Tetrahedron Lett. 2008; 49: 6364
45 Moriarty E, Aldabbagh F. Tetrahedron Lett. 2009; 50: 5251
46 Guthrie DB, Curran DP. Org. Lett. 2009; 11: 249
47 Majumdar KC, Kundu N. J. Heterocycl. Chem. 2009; 46: 492
48 Parsons AF, Wright A. Synlett 2008; 2142
49 Biswas D, Samp L, Ganguly AK. Tetrahedron Lett. 2010; 51: 2681
50 Robertson J, Palframan MJ, Shea SA, Tchabanenko K, Unsworth WP, Winters C. Tetrahedron 2008; 64: 11896
51 Zamudio-Medina A, García-González MC, Padilla J, González-Zamora E. Tetrahedron Lett. 2010; 51: 4837

52a Moreau A, Couture A, Deniau E, Grandclaudon P. Eur. J. Org. Chem. 2005; 3437
52b Kuhakarn C, Panyachariwat N, Ruchirawat S. Tetrahedron Lett. 2007; 48: 8182
52c Yamamoto Y, Kinpara K, Saigoku T, Nishiyama H, Itoh K. Org. Biomol. Chem. 2004; 2: 1287

53 Kamimura A, Ishihara Y, So M, Hayashi T. Tetrahedron Lett. 2009; 50: 1727
54 Gharpure SJ, Porwal SK. Tetrahedron Lett. 2009; 50: 7162
55 Loat Y, Petit L, Zard SZ. Chem. Commun. 2010; 5784
56 Houllier N, Lasne MC, Bureau R, Lestage P, Rouden J. Tetrahedron 2010; 66: 9231
57 Allin SM, Baron WR. S, Bowman WR, Bridge E, Elsegood MR. J, McInally T, McKee V. Tetrahedron 2008; 64: 7745
58 Li B, Tian S, Fang Z, Shi Z. Angew. Chem. Int. Ed. 2008; 47: 1115
59 Perry A, Taylor JK. Chem. Commun. 2009; 3249
60 Wipf P, Maciejewski JP. Org. Lett. 2008; 10: 4383
61 Chakraborty TK, Samanta R, Roy S, Sridhar B. Tetrahedron Lett. 2009; 50: 3306
62 Michael JP. Nat. Prod. Rep. 2008; 25: 139
63 Soriano E, Marco-Contelles J. J. Org. Chem. 2009; 74: 4061
64 Marco-Contelles J, Gomez-Sanchez E, Samadi A, Sariano E, Valderas C, Alvarez-Perez M, Carreras MC. ARKIVOC 2010; (iii): 56
65 Minozzi M, Nanni D, Spagnolo P. Chem.–Eur. J. 2009; 15: 7830
66 Zhai H, Zlotorzynska M, Sammis G. Chem. Commun. 2009; 5716
67 Zlotorzynska M, Zhai H, Sammis GM. Org. Lett. 2008; 10: 5083
68 Majumdar KC, Kundu N. J. Heterocycl. Chem. 2008; 45: 1039
69 Leemans E, D’hooghe M, Dejaegher Y, Törnroos KW, De Kimpe N. J. Org. Chem. 2008; 73: 1422
70 Godineau E, Schenk K, Landais Y. J. Org. Chem. 2008; 73: 6983
71 Pudlo M, Gerard S, Mirand C, Sapi J. Tetrahedron Lett. 2008; 49: 1066
72 Feray L, Bertrand MP. Eur. J. Org. Chem. 2008; 3164
73 Clark AJ, Wilson P. Tetrahedron Lett. 2008; 49: 4848
74 Bull JA, Hutchings MG, Lujan C, Quayle P. Tetrahedron Lett. 2008; 49: 1352

75a Gade LH, Bellemin-Laponnaz S. Top. Organomet. Chem. 2007; 21: 117
75b Roland S, Mangeney P. Top. Organomet. Chem. 2005; 15: 191
75c Clavier H, Guillemin J.-C, Mauduit M. Chirality 2007; 19: 471
75d Gillingham DG, Hoveyda AH. Angew. Chem. Int. Ed. 2007; 46: 3860

76 Dutta B, Scopelliti R, Severin K. Organometallics 2008; 27: 423
77 Martin A, Martin IP, Suarez E. Tetrahedron 2009; 65: 6147
78 Ghelfi F, Pattarozzi M, Roncaglia F, Parsons AF, Felluga F, Pagnoni UM, Valentin E, Mucci A, Bellesia F. Synthesis 2008; 3131
79 Clark A, Fullaway DR, Murphy NP, Parekh H. Synlett 2010; 610
80 Jeught SV, Vos ND, Masschelein K, Ghiviriga I, Stevens CV. Eur. J. Org. Chem. 2010; 5444
81 Yang D, Lain GY, Yang HF, Yu JD, Whang DW, Goa X. J. Org. Chem. 2009; 74: 8610
82 Yu JD, Ding W, Lian GY, Song KS, Zhang DW, Gao X, Yang D. J. Org. Chem. 2010; 75: 3232
83 Murphy JA, Schoenebeck F, Findlay NJ, Thomson DW, Zhou S, Garnier J. J. Am. Chem. Soc. 2009; 131: 6475
84 Mahesh M, Murphy JA, LeStrat F, Wessel HP. Beilstein J. Org. Chem. 2009; 5: 1
85 Jahn U, Kafka F, Pohl R, Jones PG. Tetrahedron 2009; 65: 10917
86 Mantrand N, Renaud P. Tetrahedron 2008; 64: 11860
87 Sanchez EM, Arteaga JF, Domingo V, Quílez del Moral JF, Herrador MM, Barrero AF. Tetrahedron 2008; 64: 5111
88 Sylvester KT, Chirik PJ. J. Am. Chem. Soc. 2009; 131: 8772
89 Taniguchi T, Goto N, Nishibata A, Ishibashi H. Org. Lett. 2010; 12: 112
90 Jia YX, Kundig EP. Angew. Chem. Int. Ed. 2009; 48: 1636
91 Sinan M, Ghosh K, Goswami S. J. Org. Chem. 2010; 75: 2065
92 Kim T, Kim K. Tetrahedron Lett. 2010; 51: 868
93 Crich D, Grant D. Tetrahedron Lett. 2008; 49: 2999
94 Downer-Riley NK, Jackson YA. Tetrahedron 2008; 64: 7741
95 Majumdar KC, Mondal S. Tetrahedron 2009; 65: 9604
96 Hayashi N, Hirokawa Y, Shibata I, Yasuda M, Baba A. Org. Biomol. Chem. 2008; 6: 1949
97 Zhu H, Wickenden JG, Campebell NE, Leung JC, Johnson KM, Sammis GM. Org. Lett. 2009; 11: 2019
98 Ko HM, Lee CW, Kwon HK, Chung HS, Choi SY, Chung YK, Lee E. Angew. Chem. Int. Ed. 2009; 48: 2364
99 Hartung J, Schur C, Kempter I, Gottwald T. Tetrahedron Lett. 2010; 66: 1365

100a Zhang Z, Zhang Q, Ni Z, Liu Q. Chem. Commun. 2010; 1269
100b Alcaide B, Almendros P, del Campo TM, Soriano E, Marco-Contelles JL. Chem.–Eur. J. 2009; 15: 1901
100c Leemans E, D’hooghe M, Dejaegher Y, Törnroos KW, De Kimpe N. Eur. J. Org. Chem. 2010; 352

101 Boal BW, Schammel AW, Garg NK. Org. Lett. 2009; 11: 3458

102a Pattarozzi M, Roncaglia F, Accorsi L, Parsons AF, Ghelfi F. Tetrahedron 2010; 66: 1357
102b Ram RN, Kumar N. Tetrahedron Lett. 2008; 49: 799

103 Ram RN, Kumar N, Singh N. J. Org. Chem. 2010; 75: 7408
104 Giboulot S, Luna AP, Botuha C, Ferreira F, Chemla F. Tetrahedron Lett. 2008; 49: 3963
105 Majumdar KC, Debnath P, Maji PK. Can. J. Chem. 2008; 86: 846
106 Fukuyama T, Kobayashi M, Rahman MT, Kamata N, Ryu I. Org. Lett. 2008; 10: 533
107 Kim S, Kim S. Bull. Chem. Soc. Jpn. 2007; 80: 809

108a Tzirakis MD, Orfanopoulos M. Org. Lett. 2008; 10: 873
108b Matsuo Y, Zhang Y, Nakamura E. Org. Lett. 2008; 10: 1251
108c Li F.-B, Liu T.-X, Wang G.-W. J. Org. Chem. 2008; 73: 6417
108d Clavaguera S, Khan SI, Rubin Y. Org. Lett. 2009; 11: 1389
108e Tzirakis MD, Orfanopoulos M. J. Am. Chem. Soc. 2009; 131: 4063

109 Li F.-B, Liu T.-X, Huang Y.-S, Wang G.-W. J. Org. Chem. 2009; 74: 7743

110a Powell LH, Docherty PH, Hulcoop DG, Kemmitt PD, Burton JW. Chem. Commun. 2008; 2559
110b Curry L, Hallside SM, Powell LH, Sprague SJ, Burton JW. Tetrahedron 2009; 65: 10882

111 Fujiwara SI, Shimizu Y, Makita Y, Ike TS, Kambe N. Heterocycles 2008; 76: 1577
112 Yilmaz M, Uzunalioglu N, Yakut M, Pekel AT. Turk. J. Chem. 2008; 32: 411
113 Dunach E, Esteves AP, Neves CS. S, Medeiros MJ. ECS Transactions 2008; 13: 49
114 Healy MP, Parsons AF, Rawlinson GT. Synlett 2008; 329
115 Majumdar KC, Islam R. Synth. Commun. 2008; 38: 4053
116 Bencivenni G, Lanza T, Leardini R, Minozzi M, Nanni D, Spagnolo P, Zanardi G. Org. Lett. 2008; 10: 1127
117 Singh PP, Yadav AK, Ila H, Junjappa H. J. Org. Chem. 2009; 74: 5496
118 Majumdar KC, Debnath P, Alam S, Islam R. J. Sulfur Chem. 2008; 29: 467
119 Mulholland NP, Pattenden G. Tetrahedron 2008; 64: 7400
120 Coulomb J, Certal V, Larraufie MH, Ollivier C, Corbet JP, Mignani G, Fensterbank L, Lacôte E, Malacria M. Chem.–Eur. J. 2009; 15: 10225