A New Efficient Method for the Synthesis of Fused [1,2,5]Thiadiazoles and Their Dearomatization with C‐Nucleophiles

Author:

Fedorenko Alexey K.1,Ivanova Victoria V.12,Minyaev Mikhail E.1,Bastrakov Maxim A.1,Starosotnikov Alexey M.1ORCID

Affiliation:

1. N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Leninsky prosp. 47 119991 Moscow Russia

2. Higher Chemical College RAS D.I. Mendeleev University of Chemical Technology of Russia Miusskaya sq. 9 125047 Moscow Russia

Abstract

AbstractGeneral method for the annulation of [1,2,5]thiadiazole ring to pyridine and benzene cycle has been developed using sulfur monochloride as a sulfur source. On this basis a number of [1,2,5]thiadiazolo[4,3‐b]pyridines and benzo[c]thiadiazoles were synthesized. The most π‐deficient [1,2,5]thiadiazolo[4,3‐b]pyridines readily react with neutral carbon nucleophiles such as CH‐acids, indoles, pyrrole and phloroglucinol to give 1,4‐adducts.

Publisher

Wiley

Subject

General Chemistry

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