The Journal of Organic Chemistry

Michael and Mannich reactions with benzothiazole-2-thiol

AF Halasa, GEP Smith Jr

Index: Halasa,A.F.; Smith,G.E.P. Journal of Organic Chemistry, 1971 , vol. 36, p. 636 - 641

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Citation Number: 34

Abstract

The reaction of the anion of benzothiazole-2-thiol (MBT) with activated olefins in the presence of sodium hydride with Michael reaction acceptors produced 3-substituted benzothiazoline-2-thiones. Similarly, the Mannich reaction of MBT anion with formaldehyde and primary or secondary amines produced the N-(or 3-) substituted benzothiazoline-2- thiones. Possible mechanisms and supporting nmr, ir, and uv data are discussed. The N ...