Studies on enamides. Part-7: A novel photochemical reaction pathway of N-aroyl-N-1-cyclohexenylanilines

Arkivoc

Volumn 2003, Issue 9, 2003, Pages 58-68

  Ghosh, Somnath ^a   Baul, Susmita ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

6H 5 phenyl aryl 1,2,3,4 tetrahydrophenanthridine 6 ones; N aroyl N 1 cyclohexenyl anilines; Oxidative UV irradiation; Vinyl nitrogen bond cleavage

Indexed keywords

1,2,3,4 TETRAHYDROPHENANTHRIDINE 6 ONE DERIVATIVE; 4' METHOXY 6H 5 PHENYL 1,2,3,4 TETRAHYDROPHENANTHRIDIN 6 ONE; 4',9 DIMETHOXY 6H 5 PHENYL 1,2,3,4 TETRAHYDROPHENANTHRIDIN 6 ONE; 8,9 DIMETHOXY 6H 5 PHENYL 1,2,3,4 TETRAHYDROPHENANTHRIDIN 6 ONE; 9 METHOXY 6H 5 PHENYL 1,2,3,4 TETRAHYDROPHENANTHRIDIN 6 ONE; AMIDE; ANILIDE; ANILINE DERIVATIVE; ENAMIDE DERIVATIVE; IODINE; N (2 CHLOROBENZOYL) N 1 CYCLOHEXENYLANILINE; N (2 NITROBENZOYL) N 1 CYCLOHEXENYLANILINE; N (3,4 DIMETHOXYBENZOYL) N 1 CYCLOHEXENYLANILINE; N (4 METHOXYBENZOYL) N 1 CYCLOHEXENYL 4 METHOXYANILINE; N (4 METHOXYBENZOYL) N 1 CYCLOHEXENYLANILINE; N 1 CYCLOHEXENYLANILINE DERIVATIVE; N BENZOYL N 1 CYCLOHEXENYL 4 METHOXYANILINE; N BENZOYL N 1 CYCLOHEXENYLANILINE; NITROGEN; PHENANTHRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; OXIDATION; PHOTOCHEMISTRY; REACTION ANALYSIS; ULTRAVIOLET IRRADIATION;

EID: 3042779643     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. Part 6: Ghosh, S.N.; Baul, S. Synthetic Commun. 2001, 31, 2783
2. Bertele, E.; Boos, W.; Dunitz, J.D.; Elsinger, F.; Eschenmoser, A.; Felner, I.; Gribi, H.P.; Gschwend, H.; Meyer, E.F.; Pesaro, M.; Scheffold, R. Angew. Chem. 1964, 76, 393; Angew. Chem. Int. Ed. Engl. 1964, 3, 490.
3. Bertele, E.; Boos, W.; Dunitz, J.D.; Elsinger, F.; Eschenmoser, A.; Felner, I.; Gribi, H.P.; Gschwend, H.; Meyer, E.F.; Pesaro, M.; Scheffold, R. Angew. Chem. 1964, 76, 393; Angew. Chem. Int. Ed. Engl. 1964, 3, 490.
4. Reviews: a) Sharma, R.K.; Kharasch, N. Angew. Chem. Int. Ed. Engl. 1968, 7, 36;
5. b) Lenz, Yes G.R. Synthesis 1978, 489;
6. c) Mallory, F.B.; Mallory, C.W. Org. React. 1984, 30, 1.
7. Ghosh, S.N.; Das, T.K.; Datta, D.B.; Mehta, S. Tetrahedron Lett. 1987, 28, 4611.
8. Ghosh, S.N.; Datta, D.B.; Datta, I.; Das, T.K. Tetrahedron 1989, 45, 3775.
9. Datta, I.; Das, T.K.; Ghosh, S.N. Tetrahedron Lett. 1989, 30, 4009.
10. Datta, I.; Das, T.K. (in part); Ghosh, S.N. Tetrahedron 1990, 46, 6821.
11. Ghosh, S.N.; Nandi, B.; Saima, Y. Tetrahedron Lett. 1996, 37, 3169.
12. Ghosh, S.N.; Banerjee, I.; Baul, S. Tetrahedron 1999, 55, 11537.
13. Cleveland, P.G.; Chapman, O.L. J. Chem. Soc., Chem. Commun. 1967, 1064.
14. Yang, N.C.; Shani, A.; Lenz, G.R. J. Amer. Chem. Soc. 1966, 88, 5369.
15. Lenz, G.R. J. Org. Chem. 1976, 41, 2201.
16. Ninomiya, I.; Shinohara, A.; Kiguchi, T.; Naito, T. J. Chem. Soc., Perkin Trans. 1 1976, 1868.
17. Iida, I.; Aoyagi, S.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1974, 409.
18. Ninomiya, I.; Naito, T.; Hirata, Y.; Miata, Y. J. Chem. Soc., Perkin Trans. 1 1988, 2219.
19. Ninomiya, I.; Naito, T.; Mori, T. Tetrahedron Lett. 1969, 2259.
20. Lyubarskaya, A.E.; Pauli, D.; Bren, V.; Otenkhnovich, L.P. Zh. Org. Chim. 1976, 12, 918 (Chemical Abstracts 1976, 85, 46283c).
21. Lyubarskaya, A.E.; Pauli, D.; Bren, V.; Otenkhnovich, L.P. Zh. Org. Chim. 1976, 12, 918 (Chemical Abstracts 1976, 85, 46283c).
22. The presence of an EWG such as carbonyl or a phenyl/aryl on the nitrogen atom of enamides is known to afford rearranged products (1,3- or 1,5-) on non-oxidative photolysis (vide references 3-5).
23. Heilbron, I.; Cook, A.H.; Bunbury, H.M.; Hey, D.H. Dictionary of Organic Compounds, 1965, Eyre & Spottiswoode Publishers Ltd., London.