[4+2] and [2+2] cycloaddition reactions of 1-(4-methylphenyl) and 1-benzyl-1,3-diaza-1,3-butadienes with ketenes

Tetrahedron

Volumn 53, Issue 41, 1997, Pages 14107-14114

  Rossi, Elisabetta ^a   Abbiati, Giorgio ^a   Pini, Elena ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030760132     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00912-5     Document Type: Article

References (21)

1. a Barluenga, J.; Tomas, M.; Synthesis of Heterocycles from Azadienes. In Advances in Heterocycles Chemistry; Katritzky, A. R. Ed.; Academic Press, Inc.: 1993; pp. 61-80.
2. b Büchi, G.; Galindo, J. J. Org. Chem. 1991, 56, 2605-2606.
3. c Ferguson, G.; Lough, A. J.; Mackay, D.; Weeratunga, G. J. Chem. Soc. Perkin Trans I 1991, 3361-3369.
4. d Takahashi, M.; Miyadai, S. Heterocycles 1990, 31, 883-888.
5. e Boger, D. L.; Weinreb, S. N.. In Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press; San Diego, 1987; 267-277.
6. a Hunter, D.H.; Sim, S.K. Can. J. Chem. 1972, 50, 670-677 and 678-689.
7. b Crook, S.; Sykes, P. J. Chem. Soc. Perkin Trans I 1980, 2392-2397.
8. c Mazumdar, S. N.; Mahajan, M. P. Synthesis 1990, 417-419.
9. a Matsuda, I.; Yamamoto, S.; Ishii, Y. J. Chem. Soc., Perkin Trans I 1976, 1528-1532;
10. b Mazumdar, S. N.; Ibnusaud, I.; Mahajan, M. P. Tetrahedron Lett. 1986, 27, 5875-5876;
11. c Luthardt, P.; Würthwein, E. U. Tetrahedron Lett. 1988, 29, 921-924;
12. d Ibnusaud, I.; Padma Malar, E. J.; Sundaram, N. Tetrahedron Lett. 1990, 31, 7357-7358;
13. e Singh, S. P.; Mahajan, A. R.; Prajapati, D.; Sandhu, J. S. Synthesis 1991, 1026-1028;
14. f Mazumdar, S. N.; Mahajan, M. P. Tetrahedron 1991, 47, 1473-1484;
15. g Mazumdar, S. N.; Mukherjee, S.; Sharma, A. K.; Sengupta, D.; Mahajan, M.P. Tetrahedron 1994, 50, 7579-7588.
16. a Rossi, E.; Stradi, R.; Visentin, P. Tetrahedron 1990, 46, 3581-3592, and ref. cited therein;
17. b Rossi, E.; Calabrese, D.; Farma, F. Tetrahedron 1991, 47, 5819-5834, and ref. cited therein;
18. c Rossi, E.; Pini, E. Tetrahedron 1996, 52, 7939-7946, and ref. cited therein.
19. Hunter and Sim (see ref. 2a) described the synthesis of 1b by zinc chloride-catalysed condensation of N-benzylbenzamidine and benzaldehyde, but we were unable to reproduce their results.
20. MM+ runs molecular mechanics calculation. This program is an extension of MM2 developped by Allinger and co-workers (Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127-8147) and is designed primarily for small organic molecules.
21. Luknitskii, F. I.; Vovsi, B. A: Russian Chem. Rev. 1969, 38, 487-494.