Study of the reaction of chalcone analogs of dehydroacetic acid and o-aminothiophenol: Synthesis and structure of 1,5-benzothiazepines and 1,4-benzothiazines

Tetrahedron

Volumn 61, Issue 27, 2005, Pages 6642-6651

  Prakash, Om ^a   Kumar, Ajay ^a   Sadana, Anil ^a   Prakash, Richa ^a   Singh, Shiv P ^a   Claramunt, Rosa M ^b   Sanz, Dionisia ^b   Alkorta, Ibon ^c   Elguero, José ^c  

^a KURUKSHETRA UNIVERSITY   (India)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^c INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

1,4 Benzothiazines; 1,5 Benzothiazepines; DFT calculations; GIAO chemical shifts; Tautomerism

Indexed keywords

2 THIOPHENOL; 2,3 DIHYDRO 4 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 2 (2 NITROBENZYL) 1,4 BENZOTHIAZINE; 2,3 DIHYDRO 4 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 2 (4 NITROBENZYL) 1,4 BENZOTHIAZINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (2 HYDROXYPHENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (2 NITROPHENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (2 THIENYL) 1,4 BENZOTHIAZINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (2 THIENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (3 NITROPHENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (4 HYDROXYPHENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (4 METHOXYPHENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (4 METHYLPHENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (4 N,N DIMETHYLAMINOPHENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 (4 NITROPHENYL) 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 4 PHENYL 1,5 BENZOTHIAZEPINE; 3,4 DIHYDRO 4 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 2 (4 PYRIDIN 4 YLMETHYL) 1,4 BENZOTHIAZINE; 3,4 DIHYDRO 4 (4 CHLOROPHENYL) 2 (2,4 DIOXO 6 METHYLPYRAN 3 YLIDENE) 1,5 BENZOTHIAZEPINE; ALDEHYDE; BENZOTHIAZEPINE DERIVATIVE; BENZOTHIAZINE DERIVATIVE; CARBON; CARBONYL DERIVATIVE; DEHYDROACETIC ACID; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; DRUG SYNTHESIS; NITROGEN NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 20444451689     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.035     Document Type: Article

References (43)

1. A.R. Katritzky, C.W. Rees, and E.F.V. Scriven Comprehensive Heterocyclic Chemistry II 1996 Elsevier Amsterdam
2. J.I.G. Cadogan, and S. Kulik Chem. Commun. 1973 223
3. J.B. Press, N.H. Euddy, and S.R. Safir J. Org. Chem. 45 1980 497
4. S. Pant, A. Sharma, C.K. Sharma, U.C. Pant, and A.K. Goel Indian J. Chem. 1996 794
5. G. Coispeau, and J. Elguero Bull. Soc. Chim. Fr. 1970 2717
6. J.E. Baldwin J. Chem. Soc. Chem. Commun. 1976 734
7. J.E. Baldwin, and M.J. Lusch Tetrahedron 38 1982 2939
8. S.P. Singh, M. Grover, L.S. Tarar, J. Elguero, and A. Martinez J. Heterocycl. Chem. 27 1990 865
9. S.P. Singh, D. Kumar, H. Batra, R. Naithani, I. Rozas, and J. Elguero Can. J. Chem. 78 2000 1109
10. O. Prakash, A. Kumar, and S.P. Singh J. Indian Chem. Soc. 80 2003 1
11. M. Moreno-Mañas, and R. Pleixats Adv. Heterocycl. Chem. 53 1992 1
12. O. Prakash, A. Kumar, and S.P. Singh Heterocycles 63 2004 1193
13. R.H. Wiley, C.H. Jarboe, and H.G. Ellert J. Am. Chem. Soc. 77 1955 5102
14. 15N chemical shift: see Ref. 16, p. 124.
15. G.O. Dudek, and E.P. Dudek J. Am. Chem. Soc. 88 1966 2407
16. http://www.spectroscopynow.com/Spy/tools/proton-proton.html By Stenutz, R. based on C.A.G. Haasnoot, F.A.A.M. DeLeeuw, and C. Altona Tetrahedron 36 1980 2783
17. J.B. Stothers Carbon-13 NMR Spectroscopy 1972 Academic New York
18. S. Berger, S. Braun, and H.-O. Kalinowski NMR Spectroscopy of the Non-Metallic Elements 1997 Wiley Chichester
19. A. Lévai J. Heterocycl. Chem. 41 2004 399
20. B. Djerrari, E.M. Essassi, J. Fifani, B. Garrigues, and M. Pierrot Indian J. Chem., Sect. B 42 2003 2829
21. N. Aït-Baziz, Y. Rachedi, M. Hamdi, A.M.S. Silva, F. Balegroune, R. Thierry, and N. Sellier J. Heterocycl. Chem. 41 2004 587
22. G. Negri, C. Kascheres, and A.J. Kascheres J. Heterocycl. Chem. 41 2004 461
23. Fruchier, A. ENSCM, Montpellier, France. Private communication.
24. H.C. van der Plas Ring Transformations of Heterocycles Vol. 2 1973 Academic London p 300
25. G. Salem, S.E. Filippakis, A. Hountas, and A. Terzis Acta Crystallogr. Sect. C: Cryst. Struct. Commun. C42 1986 1581
26. V. Balasubramaniyan, P. Balasubramaniyan, and A.S. Shaikh Tetrahedron 42 1986 2731
27. G. Grandolini, V. Ambrogi, and C. Rossi Eur. J. Med. Chem. 25 1990 87
28. V. Ambrogi, G. Grandolini, L. Perioli, M. Ricci, C. Rossi, and L. Tuttobello Eur. J. Med. Chem. 25 1990 403
29. T. Erker, and H. Bartsch Liebigs Ann. Chem. 1992 403
30. T. Blitzke, D. Sicker, and H. Wilde J. Heterocycl. Chem. 34 1997 453
31. H.-Z. Wang, D. Yao, R.-X. Lan, J.-X. Xu, and S. Jin Chin. Chem. Lett. 10 1999 625
32. G. Grandolini, L. Perioli, and V. Ambrogi Gazz. Chim. Ital. 127 1997 411
33. A.R. Katritzky, H.H. Odens, S. Zhang, C.J. Rostek, and O.W. Maender J. Org. Chem. 66 2001 6792
34. O. Prakash, A. Kumar, A. Sadana, and S.P. Singh Synth. Commun. 32 2002 2663
35. R.G. Parr, and W. Yang Density-Functional Theory of Atoms and Molecules 1989 Oxford, New York
36. L.J. Bartolotti, and K. Fluchick K.B. Lipkowitz D.B. Boyd Reviews in Computational Chemistry Vol. 7 1996 VCH New York 187 216
37. A.D. Becke J. Chem. Phys. 98 1993 5648
38. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
39. P.A. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213
40. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1998.
41. J.W. McIver, and A.K. Komornicki J. Am. Chem. Soc. 94 1972 2625
42. R. Ditchfield Mol. Phys. 27 1974 789
43. F. London J. Phys. Radium 8 1937 397