Versatile intramolecular aza-prins and prins cyclization of aryl epoxides: A facile synthesis of diaza-, oxa-aza-, and dioxa-bicycles

Journal of Organic Chemistry

Volumn 75, Issue 6, 2010, Pages 2081-2084

  Yadav, Jillu S ^a   Borkar, Prashant ^a   Pawan Chakravarthy, P ^a   Subba Reddy, Basi V ^a   Sarma, Akella V S ^b   Basha, Shaik Jeelani ^b   Sridhar, Balasubramanian ^c   Grée, René ^d  

^a Division of Organic Chemistry   (United States)

^b Centre for Nuclear Magnetic Resonance   (United Kingdom)

^c INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^d UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AVAILABLE P; CHEMICAL EQUATIONS; DICHLOROETHANE; FACILE SYNTHESIS; GOOD YIELD; PRINS CYCLIZATION; TRANS-SELECTIVITY;

CYCLIZATION;

PYRIDINE;

4 (4 CHLOROBENZYL)OCTAHYDRO 1,5 DITOSYL 1H PYRROLIDINO[3,2 C]PYRIDINE; 4 BBENZYLOCTAHYDRO 1 TOSYLPYRANO[4,3 B]PYRROLE; 4 BENZYL HEXAHYDRO 2H FURO[3,2 C]PYRAN; ACETALDEHYDE; ARYL EPOXIDE; DIAZA BICYCLE DERIVATIVE; DIOXA BICYCLE DERIVATIVE; EPOXIDE; OXA AZA BICYCLE DERIVATIVE; PHENYLACETALDEHYDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77949791107     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902683p     Document Type: Article

References (27)

1. (a) Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737-799.
2. (b) Bonini, C.; Righi, G. Synthesis 1994, 225-238.
3. (c) Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323-2367.
4. (d) Smith, J. G. Synthesis 1984, 629-656.
5. (a) Yadav, J. S.; Reddy, B. V. S.; Satheesh, G. Tetrahedron Lett. 2003, 44, 6501-6504.
6. Witherup, K. M.; Ransom, R. W.; Graham, A. C.; Bernard, A. M.; Salvatore, M. J.; Lumma, W. C.; Anderson, P. S.; Pitzenberger, S. M.; Varga, S. L. J. Am. Chem. Soc.1995, 117, 6682-6685.
7. Malassene, R.; Sanchez-Bajo, L.; Toupet, L.; Hurvois, J. P.; Moinet, C. Synlett 2002, 1500-1504.
8. (a) Hadden, M.; Stevenson, P. J. Tetrahedron Lett. 1999, 40, 1215-1218.
9. (b) Xia, C.; Heng, L.; Ma, D. Tetrahedron Lett. 2002, 43, 9405-9409.
10. (c) Batey, R. A.; Simoncic, P. D.; Lin, D.; Smyj, R. P.; Lough, A. J. Chem. Commun. 1999, 651-652.
11. (d) Powell, D. A.; Batey, R. A. Org. Leet. 2002, 4, 2913-2916.
12. (a) Carballo, R. M.; Ramirez, M.; Rodriguez, M. L.; Martin,V. S.; Padrón, J. L. Org. Lett. 2006, 8, 3837-3840.
13. (b) Yadav, J. S.; Reddy, B. V. S; Chaya, D. N.; Narayana Kumar, G. G. K. S.; Aravind, S.; Kunwar, A. C.; Madavi, C. Tetrahedron Lett. 2008, 49, 3330-3334.
14. (c) Yadav, J. S.; Reddy, B. V. S.; Chaya, D. N.; Narayana Kumar, G. G. K. S.; Naresh., P.; Jagadeesh, B. Tetrahedron Lett. 2009, 50, 1799-1802.
15. (d) Kishi, Y.; Nagura, H.; Inagi, S.; Fuchigami, T. Chem. Commun. 2008, 3876-3878.
16. (a) Yadav, J. S.; Rajasekhar, K.; Murty, M. S. R. Tetrahedron Lett. 2005, 46, 2311-2314.
17. (b) Yadav, J. S.; Rajasekhar, K.; Murty, M. S. R. Tetrahedron Lett. 2006, 47, 6149-6151.
18. (c) Murty, M. S. R.; Ram, K. R.; Yadav, J. S. Tetrahedron Lett. 2008, 49, 1141-1145.
19. (a)Elsworth, J. P.; Willis,C. L. Chem. Commun. 1587-1589.
20. (b) Yadav, J. S.; Chakravarthy, P. P.; Prashant, B; Reddy, B. V. S.; Sarma, A. V. s. Tetrahedron Lett. 2009, 50, 5998-6000.
21. Giacometti, L.; Wolf, N.; Gomzi, Z.; Milin, C. React. Kinet. Catal. Lett. 1996, 59, 235-240.
22. (a) Filippi, J.-J.; Duñach, E.; Fernandez, X.; Meierhenrich, U. J. Tetrahedron 2008, 42, 9999-10003.
23. (b) Karodia, N.; Liu, X.; Ludley, P.; Pletsas, D.; Stevenson, G. Tetrahedron 2006, 48, 11039-11043.
24. (c) Koulouri, S.; Malamidou-Xenikaki, E.; Spyroudis, S. Tetrahedron 2005, 52, 10894-10902.
25. (a) Yadav, J. S.; Thrimurtulu, N.; Gayathri, K. U.; Reddy, B. V. S.; Prasad, A. R. Tetrahedron Lett. 2008, 49, 6617-6620.
26. (b) Yadav, J. S.; Lakshmi, K. A.; Reddy, N. M.; Prasad, A. R.; Reddy, B. V. S. Tetrahedron 2010, 44, 334-338.
27. (c) Yadav, J. S.; Padmavani, B.; Reddy, B. V. S.; Venugopal, Ch.; Rao, A. B. Synlett 2007, 2045-2048.