Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S⋯O interactions

Tetrahedron

Volumn 63, Issue 9, 2007, Pages 1937-1945

  Rašović, Aleksandar ^a   Steel, Peter J ^b   Kleinpeter, Erich ^c   Marković, Rade ^a,d  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF CANTERBURY   (New Zealand)

^c UNIVERSITY OF POTSDAM   (Germany)

^d UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

1,2 Dithioles; 1,3 Thiazines; Non bonded S O interaction; Rearrangement; Thiazolidines

Indexed keywords

1,3 THIAZINE DERIVATIVE; DITHIOL DERIVATIVE; OXYGEN; REAGENT; SULFUR; THIAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; METHODOLOGY; MOLECULAR INTERACTION; PRECURSOR; PRIORITY JOURNAL; REDUCTION; RING OPENING; SYNTHESIS;

EID: 33846417967     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.075     Document Type: Article

References (38)

1. Nagao Y., Honjo T., Iimori H., Goto S., Sano S., Shiro M., Yamaguchi K., and Sei Y. Tetrahedron Lett. 45 (2004) 8757-8761
2. Meyer E., Joussef A.C., Gallardo H., Bortoluzzi A.J., and Longo R.L. Tetrahedron 59 (2003) 10187-10193
3. Wu S., and Greer A. J. Org. Chem. 65 (2000) 4883-4887
4. Rábai J., Kapovits I., Jalsovszky I., Argay Gy., Fülöp V., Kálmán A., and Koritsánszky T. J. Mol. Struct. 382 (1996) 13-21
5. Ogurtsov V.A., Rakitin O.A., Rees C.W., Smolentsev A.A., Belyakov P.A., Golovanov D.G., and Lyssenko K.A. Org. Lett. 7 (2005) 791-794
6. Ángyán J.G., Poirier R.A., Kucsman A., and Csizmadia I.G. J. Am. Chem. Soc. 109 (1987) 2237-2245 and references cited therein
7. Kakusawa N., Tobiyasu Y., Yasuike S., Yamaguchi K., Seki H., and Kurita J. Tetrahedron Lett. 44 (2003) 8589-8592
8. Stojanović M., Baranac M., and Marković R. Synlett (2006) 729-732
9. Marković R., Baranac M., Steel P., Kleinpeter E., and Stojanović M. Heterocycles 65 (2005) 2635-2647
10. Marković R., Baranac M., and Jovetić S. Tetrahedron Lett. 44 (2003) 7087-7090
11. Preliminary communication: Marković, R.; Rašović, A. 22nd International Symposium on the Organic Chemistry of Sulfur. Aug. 20-25, 2006, Saitama, Japan, Book of Abstracts, p 38.
12. Marković R., Baranac M., D{combining short stroke overlay}ambaski Z., Stojanović M., and Steel P.J. Tetrahedron 59 (2003) 7803-7810
13. For a review regarding the Lawesson's reagent, see:
14. Cava M.P., and Levinson I.M. Tetrahedron 41 (1985) 5061-5087
15. Cherkasov R.A., Kutyrev G.A., and Pudovik A.N. Tetrahedron 41 (1985) 2567-2624
16. Jesberger M., Davis T.P., and Barner L. Synthesis (2003) 1929-1958
17. New oxodithioles 10b,c were also synthesized independently from 1,2-dithioles 8b,c according to procedure reported by. Ammick G., and Vialle J. Bull. Soc. Chim. Fr. (1971) 4002-4006
18. Lozac'h N. In: Katritzky A.R., Rees C.W., and Potts K.T. (Eds). Comprehensive Heterocyclic Chemistry Vol. 6 (1984), Pergamon, Oxford 1049-1070
19. Perrin C.L., Kim Y.-J., and Kuperman J. J. Phys. Chem. A 105 (2001) 11383-11387
20. Spanget-Larsen J., and Andersen K.B. Phys. Chem. Chem. Phys. 3 (2001) 908-916
21. Bjernemose J.K., Frandsen E., Jensen F., and Pedersen C.Th. Tetrahedron 59 (2003) 10255-10259
22. Potts K.T., Nye S.A., and Smith K.A. J. Org. Chem. 57 (1992) 3895-3901
23. Zhang W., and Henry Y. Synlett (2001) 1129-1130
24. Pedersen B.S., and Lawesson S.-O. Tetrahedron 35 (1979) 2433-2437
25. McKinnon D.M. In: Katritzky A.R., Rees C.W., and Potts K.T. (Eds). Comprehensive Heterocyclic Chemistry Vol. 6 (1984), Pergamon, Oxford 783-811
26. The ab initio calculations were performed on SGI Octane and SGI Origin 2000 workstations and a Linux cluster using the program GAUSSIAN 03:. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A., Vreven Jr. T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
27. ** level of theory without restrictions; see:. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab initio Molecular Orbital Theory (1986), Wiley, New York, NY
28. Klod S., and Kleinpeter E. J. Chem. Soc., Perkin Trans. 2 (2001) 1893-1898
29. Chen Z., Wannere C.S., Corminboeuf C., Puchta R., and Schleyer P.v.R. Chem. Rev. 105 (2005) 3842-3888
30. Ditchfield J.R. Mol. Phys. 27 (1974) 789-807
31. Cheeseman J.R., Trucks G.W., Keith T.A., and Frisch M.J. J. Chem. Phys. 104 (1996) 5497-5509
32. Yokoyama M., Shiraishi T., Hatanaka H., and Ogata K. J. Chem. Soc., Chem. Commun. (1985) 1704-1705
33. Kobayashi K., Masu H., Shuto A., and Yamaguchi K. Chem. Mater. 17 (2005) 6666-6673 and references therein
34. 4-trithiapentalenes, the X-ray study shows that the central C(2)-S(2) bond is actually longer than the C(1)-S(1) and C(4)-S(3) bonds, which implies its lower double bond character.
35. Čmelik R., Čajan M., Marek J., and Pazdera P. Collect. Czech. Chem. Commun. 68 (2003) 1243-1263
36. For photochemical rearrangement of 4-methyl substituted 2,3-dihydro-6H-1,3-thiazine to thiazolidine derivative, via an acyclic intermediate, see:. Bhatia S.H., Buckley D.M., McCabe R.W., Avent A., Brown R.G., and Hitchcock P.B. J. Chem. Soc., Perkin Trans. 1 (1998) 569-574
37. Sheldrick G.M. Acta Crystallogr., Sect. A 46 (1990) 467-473
38. Sheldrick G.M. SHELXTL (1997), Bruker Analytical X-ray Systems