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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 York
Novel 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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