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Synthesis of heterocyclic Compounds, XXXVII. Preparation of 4,6-Diaryl-1,2-dihydro-2-thioxo-3,5-pyridinedicarbonitriles and Related Compounds

✍ Scribed by Encinas, María Jesús Rubio ;Seoane, Carlos ;Soto, José L.

Publisher
John Wiley and Sons
Year
1984
Tongue
English
Weight
461 KB
Volume
1984
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The reaction of cyanothioacetamide (1) with α‐benzoylcinnamonitriles 2 in basic ethanolic solution leads to 4,6‐diaryl‐1,2‐dihydro‐2‐thioxo‐3,5‐pyridinedicarbonitriles 3 together with the disulfides 4. Treatment of 4 with 2‐mercaptoethanol causes transformation into 3 which can lead to 4 upon reaction with either iodine‐potassium iodide or dimethyl sulfoxide‐trifluoroacetic acid. Methylation of 3 or 4 yields the expected methylthiopyridines 5. On the other hand, reaction of 3 with methyl chloroacetate allows the preparation of thieno[2,3‐b]pyridines 8.

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## Abstract The reaction of 2‐chloro‐4‐(methylsulfonyl)benzoyl chloride (5) with 1‐methyl‐1__H__‐2,1‐benzothiazin‐4‐(3__H__)‐one 2,2‐dioxide (4) gave the __O__‐benzoyl compound, 1‐methyl‐2,2‐dioxido‐1__H__‐2,1‐benzothiazin‐4‐yl 2‐chloro‐4‐(methylsulfonyl)benzoate (6), which rearranged to give the C