1-Bis(methoxy)-4-bis(methylthio)-3-buten-2-one: Useful three carbon synthon for synthesis of five and six membered heterocycles with masked (or unmasked) aldehyde functionality

Tetrahedron

Volumn 59, Issue 15, 2003, Pages 2631-2639

  Mahata, Pranab K ^a   Syam Kumar, U K ^a   Sriram, V ^a   Ila, H ^a   Junjappa, H ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Heterocyclic aldehydes; Heterocyclization; Pyruvaldehye dimethylacetal; oxoketene dithioacetals

Indexed keywords

1 BIS(METHOXY) 4 BIS(METHYLTHIO) 3 BUTEN 2 ONE; 2 (METHYLTHIO)THIOPEN 4 ALDEHYDE; 3 [BIS(METHOXY)METHYL] 5 (METHYLTHIO)ISOXAZOLE; 3(5) (METHOXY)METHYL 5(3) (METHYLTHIO)PYRAZOLE; 3(5) (METHYLTHIO)PYRAZOL 5(3) ALDEHYDE; 3(5) [BIS(METHOXY)METHYL] 5(3) (1 N MORPHOLINO)PYRAZOLE; 3(5) [BIS(METHOXY)METHYL] 5(3) (1 N PIPERIDINO)PYRAZOLE; ALDEHYDE; ALDEHYDE DERIVATIVE; CARBENE; COPPER ION; DIPYRONE; GUANIDINE; HETEROCYCLIC COMPOUND; HYDRAZINE; HYDROXYLAMINE; ISOXAZOLE; KETONE DERIVATIVE; PYRAZOLE; PYRIDINE; PYRIMIDINE; THIOUREA; UNCLASSIFIED DRUG; ZINC ION;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; POLYMERIZATION; PRIORITY JOURNAL; SIMMONS SMITH REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037424845     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00332-6     Document Type: Article

References (46)

1. (a) Comins D.L., Nolan J.M. Org. Lett. 3:2001;4255
2. (b) Kurata H., Nakaminami H., Matsumoto K., Kawase T., Oda M. Chem. Commun. 2001;529
3. (c) Patra A., Batra S., Kundu B., Joshi B.S., Roy R., Bhaduri A.P. Synthesis. 2001;276
4. (d) Felpin F.-X., Girard S., Vo-Thanh G., Robins R.J., Villieras J., Lebreton J. J. Org. Chem. 66:2001;6305
5. (e) Wang W., Xiong C., Yang J., Hruby V.J. Tetrahedron Lett. 42:2001;7717
6. (f) Noguchi M., Sakamoto K., Nagata S., Kajigaeshi S. J. Heterocycl. Chem. 25:1988;205.
7. (a) Meth-Cohn O., Tarnowski B. Katritzky A.R. Advances in Heterocyclic Chemistry. Vol. 31:1982;207-236 Academic, New York,
8. (b) Meth-Cohn O., Stanforth S.P. Trost B.M. Comprehensive Organic Synthesis. Vol. 2:1991;777-794 Pergamon, Oxford,
9. (c) Rudloff I., Michalik M., Montero A., Peseke K. Synthesis. 2001;1686.
10. Chackalamannil S., Davies R. Org. Lett. 3:2001;1427.
11. (a) Frey L.F., Marcantonio K., Frantz D.E., Murry J.A., Tillyer R.D., Grabowski E.J.J., Reider P.J. Tetrahedron Lett. 42:2001;6815
12. (b) Nicolaou K.C., Huang X., Giuseppone N., Rao P.B., Bella M., Reddy M.V., Snyder S.A. Angew. Chem. Int. Ed. Engl. 40:2001;4705.
13. (a) Brown D.J. Katritzky A.R., Rees C.W. Comprehensive Heterocyclic Chemistry. Vol. 3:1984;125 Pergamon, Oxford. Part 2B
14. (b) Mizzoni R.H. Abramovitch R.A. Chemistry of Heterocyclic Compounds, Pyridine and its Derivatives. Vol. 14:1975;116-118 Wiley, New York. Suppl. Part IV
15. (c) Hartough H.D. Chemistry of Heterocyclic Compounds. 1952;Interscience, New York. pp 307-311.
16. (a) Abdallah H., Gree R. Tetrahedron Lett. 21:1980;2239
17. (b) Piantadosi C., Skulason V.G., Irvin J.L., Powell J.M., Hall L. J. Med. Chem. 7:1964;337
18. (c) Baker B.R., Jordaan J.H. J. Heterocycl. Chem. 4:1967;31
19. (d) Bredereck H., Sell R., Effenberger F. Chem. Ber. 97:1964;3407.
20. (a) Review: Junjappa H., Ila H., Asokan C.V. Tetrahedron. 46:1990;5423
21. (b) Ila H., Junjappa H., Mohanta P.K. Gribble G.W., Gilchrist T.L. Progress in Heterocyclic Chemistry. Vol. 13:2001;1-24 Pergamon, Oxford,
22. (c) Suresh J.R., Syam Kumar U.K., Ila H., Junjappa H. Tetrahedron. 57:2001;781. and references therein
23. (d) Suresh J.R., Barun O., Ila H., Junjappa H. Tetrahedron. 56:2000;8153. and references therein
24. (e) Barun O., Patra P.K., Ila H., Junjappa H. Tetrahedron Lett. 40:1999;3797
25. (f) Basaveswara Rao M.V., Syam Kumar U.K., Ila H., Junjappa H. Tetrahedron. 55:1999;11563
26. (g) Barun O., Ila H., Junjappa H., Singh O.M. J. Org. Chem. 65:2000;1583
27. (h) Kishore K., Reddy K.R., Suresh J.R., Ila H., Junjappa H. Tetrahedron. 55:1999;7645.
28. Chauhan S.M.S., Junjappa H. Synthesis. 1975;798.
29. Purkayastha M.L., Ila H., Junjappa H. Synthesis. 1989;20.
30. Singh O.M., Junjappa H., Ila H. J. Chem. Soc., Perkin Trans. 1. 1997;3561.
31. Giardina G.A.M., Sarau H.M., Farina C., Medhurst A.D., Grugni M., Raveglia L.F., Schmidt D.B., Rigolio R., Luttmann M., Vecchietti V., Hay D.W.P. J. Med. Chem. 40:1997;1794.
32. (a) Bhat L.N., Thomas A., Ila H., Junjappa H. Tetrahedron. 48:1992;10377
33. (b) Thomas A., Singh G., Ila H., Junjappa H. Tetrahedron Lett. 30:1989;3093
34. (c) Bhat L.N., Ila H., Junjappa H. Synthesis. 1993;959.
35. Rajappa S. Katritzky A.R., Rees C.W. Comprehensive Heterocyclic Chemistry. Vol. 4:1984;759 Pergamon, Oxford. Part 3.
36. (a) Chauhan S.M.S., Junjappa H. Synthesis. 1974;880
37. (b) Chauhan S.M.S., Junjappa H. Tetrahedron. 32:1976;1779.
38. (a) Rastogi R.R., Kumar A., Ila H., Junjappa H. J. Chem. Soc., Perkin Trans. 1. 1978;549
39. (b) Rastogi R.R., Ila H., Junjappa H. J. Chem. Soc., Chem. Commun. 1975;645.
40. Gupta A.K., Ila H., Junjappa H. Tetrahedron. 46:1990;3703.
41. (a) Troschutz R., Heinemann O., Waibel R., Troschutz J. Arch. Pharm. 328:1995;557
42. (b) Falbe J. Houben-Weyl, Methoden der Organischen Chemie. 1983;231 Thieme, Stuttgart. Band E3.
43. (a) Kao B.C., Doshi H., Reyes-Rivera H., Titus D.D., Yin M., Dalton D.R. J. Heterocycl. Chem. 28:1991;1315
44. (b) Rimek H.-J. Liebigs Ann. Chem. 670:1963;69.
45. Niu C., Li J., Doyle T.W., Chen S.H. Tetrahedron. 54:1998;6311.
46. Graf E., Troschutz R. Synthesis. 1999;1216.