Reactions of 1,3-diazabuta-1,3-dienes with ketenes: How crucial are thesteric factors/conformational preferences in influencing reaction pathways?

Arkivoc

Volumn 2002, Issue 7, 2002, Pages 106-115

  Marwaha, Alka ^a   Anand, Amit ^a   Kumar, R Senthil ^a   Mahajan, M P ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

1,3 Diazabuta 1,3 dienes; Ab initio and DFT calculations; Azetidinones; Conformational preferences; Dihydropyrimidinones

Indexed keywords

1 BENZYL 2 METHYLTHIO 4,4 DIPHENYL 1,3 DIAZABUTA 1,3 DIENE; 1,4,4 TRIPHENYL 2 METHYLTHIO 1,3 DIAZABUTA 1,3 DIENE; 3 BENZYL 5,5,6,6, TETRAPHENYL 2 METHYLTHIO 3,4,5,6 TETRAHYDROPYRIMIDIN 4 ONE; 3 BENZYL 5,6,6 TRIPHENYL 2 METHYLTHIO 3,4,5,6 TETRAHYDROPYRIMIDIN 4 ONE; 3,5,5,6,6 PENTAPHENYL 2 METHYLTHIO 3,4,5,6 TETRAHYDROPYRIMIDIN 4 ONE; 3,5,6,6 TETRAPHENYL 2 METHYLTHIO 3,4,5,6 TETRAHYDROPYRIMIDIN 4 ONE; 4 PYRIMIDINONE DERIVATIVE; BENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONFORMATION; CYCLOADDITION; METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 3242658199     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. (a) Valenti, E.; Pericas, M.A.; Mayana, A. J. Org. Chem. 1990, 55, 3582.
2. (b) Wang, X.; Houk, K. N. J. Org. Chem. 1990, 112, 1754.
3. (c) Yambe, S.; Minato, T.; Osamura, Y. J. Am. Soc. 1993, 450.
4. (d) Bernadi, F.; Bottoni, A.; Robb, M. A.; Venturini, A. J. Am. Chem. Soc. 1990, 112, 2106.
5. (a) Lynch, J. E.; Riseman, S. M.; Laswell, W. L.; Tschaen, D. M.; Volante, R. P.; Smith, G. B.; Shinkay, I. J. Org. Chem. 1989, 54, 3792.
6. (b) Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995.
7. (c) Lopez, R.; Sordo, J. A.; Gonzalez, J. J. Org. Chem. 1993, 58, 7036.
8. (d) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085.
9. (e) Arrieta, A.; Ugalde, J. M.; Cossio, F. P.; Lecea, B. Tetrahedron Lett. 1994, 35, 4465.
10. (f) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869.
11. (g) Staudinger, M. Liebigs. Ann. Chem., 1907, 356, 51.
12. (a) Tidwell, T. T. Ketenes, Wiley: New York, 1995.
13. (b) Tidwell, T. T. Acc. Chem. Res. 1990, 23, 273.
14. (c) Hyatt, J. A.; Raynolds, P. W. Org. React. 1994, 45, 159.
15. (c) Huisgen, R.; Otto, P., Tetrahedron Lett. 1968, 43, 4491.
16. (d) Huisgen, R.; Otto, P. Chem. Ber. 1969, 102, 3475.
17. (d) The Chemistry of Ketenes, Allenes and Related Compounds. In The Chemistry of Functional Groups; Patai, S. Ed., Wiley: Chichester, U.K., 1980, Parts 1 and 2.
18. (e) Bellus, D.; Ernst, B. Angew. Chem. Int. Ed. Engl. 1988, 27, 797 and the references cited therein.
19. (f) Jayakumar, S.; Ishar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379-471.
20. (a) Durckheimer, W.; Blumback, J.; Lattrell, R.; Sheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180.
21. (b) Brady, W. T.; Gu, Y. J. Org. Chem. 1989, 54, 2834-2838.
22. (c) Alcaide, B.; Camtalego, Y. M.; Plumet, J.; Lopez, J. R.; Sierra, M. A. Tetrahedron Lett. 1991, 32, 803.
23. (a) Matsuda, I.; Yamamoto, S.; Ishii, Y. J. Chem. Soc., Perkin Trans 1, 1976, 1523-1528.
24. (b) Luthardt, P.; Wurthwein, E.-U. Tetrahedron Lett. 1988, 29, 921.
25. (c) Luthardt, P.; Moller, M. H.; Rodewald, U.; Wurthwein, E.-U. Chem. Ber. 1989, 122, 1705.
26. (d) Rossi, E.; Abbiatti, G.; Pini, E.; Tetrahedron 1997, 53, 14107.
27. (a) Mazumdar, S. N.; Ibnusaud, I.; Mahajan, M. P. Tetrahedron Lett. 1986, 27, 5875.
28. (b) Mazumdar, S. N.; Mahajan, M. P. Tetrahedron 1991, 47, 1473.
29. (c) Mazumdar, S. N.; Mukherjee, S.; Sharma, A. K.; Sengupta, D.; Mahajan, M. P. Tetrahedron 1994, 50, 7579.
30. (d) Mukherjee, S.; Mazumdar S. N.; Sharma, A. K.; Mahajan, M. P. Heterocycles 1998, 47, 933.
31. (e) Dey, P. D.; Sharma, A. K.; Bharatam, P. V.; Mahajan, M. P. Tetrahedron 1997, 53, 13829.
32. (f) Mazumdar, S. N.; Mahajan, M. P. Synthesis 1990, 417.
33. (g) Sharma, A. K.; Mahajan, M. P. Heterocycles 1995, 40, 787.
34. (h) Dey, P. D.; Sharma, A. K.; Rai, S. N.; Mahajan, M. P. Tetrahedron 1995, 51, 7459.
35. Kumar, R. Senthil, Ph.D thesis, Dept. of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar, submitted.
36. (a) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory, Wiley-Interscience: New York, 1986.
37. (b) Foresman, J. B.; Frisch, E. Exploring Chemistry with Electronic Structure Methods (2nd edition) Gaussian Inc. Pittsburgh.
38. (c) Bartolotti, L. J.; Fluchick, K. In, Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B. Eds; VCH Publishers: New York, 1996: vol. 7, pp 187-216.
39. (d) Pare, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford: New York, 1989.
40. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
41. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
42. (a) Marwaha, A.; Kumar, R. S.; Bharatam, P. V.; Mahajan, M. P. Theochem (Accepted).
43. (b) Bharatam, P. V.; Kumar, R. S.; Mahajan, M. P. Org. Lett. 2000, 2, 2725-2728 and the references cited therein.
44. th ed.; Longman Singapore Publishers Pte. Ltd.
45. Stevens, C. L.; French, J. C. J. Am. Chem. Soc. 1953, 75, 657.