Synthesis of heterocyclic compounds from o‐aminobenzenethiol and ammonium thiocarbamate

Abstract

The reaction of o‐aminobenzenethiol with carbonyl sulfide in the presence of triethylamine afforded an alternate route for the synthesis of 2‐benzothiazolinone (1) in 97–98% yield. The reaction of ammonium thiocarbamate (2) with 2‐chlorocyclohexanone furnished the novel 4,5,6,7‐tetrahydro‐2‐benzothiazolinone (3). 3‐Ethoxy‐2H‐1,4‐benzothiazin‐2‐one (7) was prepared by the reaction of o‐aminobenzenethiol with diethyl oxalate. Possible pathways and supporting nmr, ir and mass spectra are discussed.

Copper(I)‐Catalyzed Cascade Synthesis of 2‐Substituted 1,3‐Benzothiazoles: Direct Access to Benzothiazolones

“…Additionally, the benzothiazolone core structure can be found in a large number of compounds having a range of biological activities as progesterone receptor (PR) antagonists,1i fungicides, and herbicides. [3a–c] Traditionally they are synthesized by the condensation of 2‐aminothiophenol with ethyl chloroformate,17a urea,17b ammonium thiocarbamate,17c or disuccinimido carbonate 17d. Methods are also available for the preparation of benzothiazolones using precursors such as 2‐chloro‐1,3‐benzothiazole and 2‐benzothiazolylalkyl sulfide.…”

Convenient synthesis and characterization of some novel benzothiazolone-based Schiff bases as potential pharmaceutically active agents

“…The identity of the known products 2(3H)-benzothiazolone derivatives 1, 2, 3a, 3b, 4a and 4b was confirmed by the comparison of their melting points and spectroscopic data with those of authentic compounds available in the literature. [35][36][37][38][39][40] General procedure for the preparation of nitro compounds (3a-3b):…”

Organocatalytic Cyclization of COS and Propargylic Derivatives to Value‐Added Heterocyclic Compounds

“…Carbonyl sulfide (COS), as a triatomic molecule possessing a carbonyl group double bonded to a sulfur atom, is the most significant compound in the global sulfur cycle, which is emitted from volcanoes and deep sea vents. [12] Early studies mainly relied on the ethanolamine, 2-aminobenzenethiol, 2-chloroethylamine or propargylic amides as substrates to react with COS in stochiometric manner, [13] only generating the structurally simple thiazolidinone (Scheme 1, I and II). [12] Early studies mainly relied on the ethanolamine, 2-aminobenzenethiol, 2-chloroethylamine or propargylic amides as substrates to react with COS in stochiometric manner, [13] only generating the structurally simple thiazolidinone (Scheme 1, I and II).…”