An efficient synthesis of highly substituted pyrroles from β-oxodithiocarboxylates

α-Oxoketene- N, S-acetals, prepared by the reaction of alkyl glycinate hydrochlorides with β-oxodithiocarboxylates followed by alkylation, underwent cyclization in presence of chloromethyleneiminium salt derived from POCl 3/DMF to afford alkyl-3-aryl-4-formyl-5-(alkylsulfanyl)-1 H-pyrrole-2-carboxyl...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2006-02, Vol.62 (8), p.1708-1716
Main Authors: Mathew, Paulson, Asokan, C.V.
Format: Article
Language:English
Subjects:
Dithiocarboxylates
Ketene- N, S-acetals
Pyrroles
Vilsmeier–Haack reagent
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:α-Oxoketene- N, S-acetals, prepared by the reaction of alkyl glycinate hydrochlorides with β-oxodithiocarboxylates followed by alkylation, underwent cyclization in presence of chloromethyleneiminium salt derived from POCl 3/DMF to afford alkyl-3-aryl-4-formyl-5-(alkylsulfanyl)-1 H-pyrrole-2-carboxylates in excellent yields. Alkyl-3-aryl-5-(alkylsulfanyl)-1 H-pyrrole-2-carboxylates were formed in moderate yields when the same N, S-acetals were treated with DBU. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.11.076