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Synthesis 2003(7): 1079-1082
DOI: 10.1055/s-2003-39179
DOI: 10.1055/s-2003-39179
PAPER
© Georg Thieme Verlag Stuttgart ˙ New YorkNovel Chemoselective Annulation of Imidazole and 1,2,4-Thiadiazine Rings on Azoles Involving Acid Labile Methanesulfinyl Group
Further Information
Received
3 February 2003
Publication Date:
09 May 2003 (online)
Publication History
Publication Date:
09 May 2003 (online)
Abstract
Oxa(thia)diazole adducts 2a-d, DMSO and azole Schiff bases 1a-d are chemoselectively annulated with sulfuric acid, acetic acid, and thionyl chloride to yield imidazo[2,1-b]-1,3,4-oxa(thia)diazoles 3a-d. Their 5-methylsulfenyl analogues 4a-d and 1,3,4-oxa(thia)diazolo[3,2-b]-1,2,4-thiadiazines 5a-d, respectively, 3-5 are formed via demethylsulfinylation, the Pummerer rearrangement, and deoxygenative demethylation, in a one-pot procedure.
Key words
chemoselective synthesis - Pummerer rearrangement - Schiff bases - imidazoles - 1,3,4-oxa(thia)diazoles - 1,2,4-thiadiazines
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Arranz ME.Diaz JA.Ingate ST.Witvrouw M.Pannecouque C.Balzarini J.Clercq ED.Vega S. Bioorg. Med.Chem. 1999, 7: 2811 - 2
Arranz ME.Diaz JA.Ingate ST.Witvrouw M.Pannecouque C.Balzarini J.Clercq ED.Vega S. J. Med. Chem. 1998, 41: 4109 - 3
Neilla CG.Prestona PN.Wightmana RH. Tetrahedron 1998, 54: 13645 - 4
Badger AM.Bradbeer JN.Votta B.Lee JC.Adams JL.Griswold DE. J. Pharmacol. Exp. Ther. 1996, 279: 1453 - 5
Shilcrat SC.Mokhallalati MK.Fortunak JMD.Pridgen LN. J. Org. Chem. 1997, 62: 8449 - 6
Makino K.Sakata G.Morimoto K.Ochiai Y. Heterocycles 1985, 23: 2025 - 7
Collis AJ.Foster ML.Halley F.Maslen C.McLay IM.Page KM.Redford EJ.Souness JE.Wilsher NE. Bioorg. Med. Chem. Lett. 2001, 11: 693 - 8
- 9
Slee DH.Romano SJ.Yu J.Nguyen TN.John JK.Raheja NK.Axe FU.Jones TK.Ripka WC. J. Med. Chem. 2001, 44: 2094 - 10
Callahan JF.Burgess JL.Fornwald JA.Gaster LM.Harling JD.Harrington FP.Heer J.Kwon C.Lehr R.Mathur A.Olson BA.Weinstock J.Laping NJ. J. Med. Chem. 2002, 45: 999 - 11
Yadav LDS.Kapoor R. Synthesis 2002, 1502 - 12
Yadav LDS.Sharma S. Synthesis 1993, 864 - 13
Yadav LDS.Vaish A. J. Chem. Res., Synop. 1993, 508 - 14
Russel GA.Ochrymowycz LA. J. Org. Chem. 1970, 35: 764 - 15
Moore TL. J. Org. Chem. 1967, 32: 2786 - 16
Russel GA.Mikol GJ. J. Am. Chem. Soc. 1966, 88: 5498 - 17
Corey EJ.Chaykovsky M. J. Am. Chem. Soc. 1965, 87: 1345 - 18
Rosowsky A.Chen KKN. J. Org. Chem. 1973, 38: 2073 - 19
Singh H.Yadav LDS.Sharma KS.Chaudhary JP. Acta Chim. Hung. 1984, 115: 377 - 20
Singh H.Yadav LDS.Sharma KS. Indian J. Chem., Sect. B 1982, 21: 480