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Syntheses of potassium 1,1-dioxopyrido[4,3-e]-1,4,2-dithiazine-3-thiolate and its application to the synthesis of novel sulfonamides with potential biological activity

✍ Scribed by Zdzislaw Brzozowski; Franciszek Sâczewski; Jaroslaw Slawiński

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
437 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Potassium 1,1‐dioxopyrido[4,3‐e]‐1,4,2‐dithiazine‐3‐thiolate 2 has been synthesized and applied to the syntheses of 7__H__‐1,1‐dioxopyrido[4,3‐e]‐1,4,2‐dithiazolium‐3‐thiolate 3 and 3‐methylthiopyrido[4,3‐e]‐1,4,2‐dithiazine 1,1‐dioxide 4 which provided easy access to a variety of its 3‐amino derivatives 5‐10. Hydrazinolysis of 7, 8 and 10 afforded the corresponding 3‐amino‐2‐(1,4‐dihydro‐4‐thioxopyrid‐3‐ylsulfonyl)guanidines 11‐13. Subsequent reaction of 12 with 4‐chlorobenzaldehyde gave condensation product 14. 1,4‐Dihydro‐2‐thioxopyridine‐3‐sulfonamide 15 was also prepared from the potassium salt 2 upon alkaline hydrolysis, whereas alkylation of 15 gave the appropriate S‐substituted derivatives 16‐19 or S,N‐disubstituted compounds 20‐21.

📜 SIMILAR VOLUMES

Application of 3-methylthiopyrido[4,3-e]
Application of 3-methylthiopyrido[4,3-e]-1,4,2-dithiazine 1,1-dioxide to the synthesis of novel series of 4H-pyrido[4,3-e]-1,2,4-thiadiazine derivatives with potential biological activity
✍ Zdzisław Brzozowski; Jarosław Sławiński; Anna Kędzia; Ewa Kwapisz; Maria Gdaniec 📂 Article 📅 2009 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 252 KB

## Abstract magnified image Two series of 4__H__‐pyrido[4,3‐__e__]‐1,2,4‐thiadiazine derivatives **3**, **4**, **5** and **7**, **8**, **9**, **10**, **11**, **12** were synthesized by the reactions of 3‐methylthiopyrido[4,3‐__e__]‐1,4,2‐dithiazine 1,1‐dioxide **1** with 2‐or 6‐hydrazinoazines and