Volume 19, Issue 7
Heterocyclic Compounds
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ChemInform Abstract: Ketene-S,N-acetals as Synthetic Intermediates for Heterocycles. New Synthesis of Multisubstituted Pyridine-2-thiones.

H. TAKAHATA

H. TAKAHATA

Fac. Pharm. Sci., Toyama Med. &Pharm., Univ., Toyama 930-01, Japan

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E.-C. WANG

E.-C. WANG

Fac. Pharm. Sci., Toyama Med. &Pharm., Univ., Toyama 930-01, Japan

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T. NAKAJIMA

T. NAKAJIMA

Fac. Pharm. Sci., Toyama Med. &Pharm., Univ., Toyama 930-01, Japan

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T. YAMAZAKI

T. YAMAZAKI

Fac. Pharm. Sci., Toyama Med. &Pharm., Univ., Toyama 930-01, Japan

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First published: February 16, 1988

Abstract

Coupling of malodinitrile (II) with the ketene-S,N-acetals (I) and (V) yields the β-dicyanomethylene thioamides (III) and (VI) which are cyclized under basic conditions to form the pyridinethiones (IV) or (VII).

ChemInform Abstract

Coupling of malodinitrile (II) with the ketene-S,N-acetals (I) and (V) yields the β-dicyanomethylene thioamides (III) and (VI) which are cyclized under basic conditions to form the pyridinethiones (IV) or (VII). Metalation of (IIIa) with butyllithium yields the intermediate (VIII) which is directly alkylated with the halides (IX) to give the pyridinethiones (X).

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