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Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

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Reagent-Controlled Chemodivergent Approach to Thiazolines and Thiazines from α-N-Hydroxyimino Dithioesters

Published:9 August 2022 DOI: 10.1002/adsc.202200511
Subhasish Ray, Saurabh Singh, Ganesh Kumar, Gaurav Shukla, Maya Shankar Singh

Abstract

A chemoselective route to thiazolines and thiazines has been devised by heterocyclization of viable α-N-hydroxyimino-β-oxodithioesters with 2-chloroethylamine hydrochloride/3-chloropropylamine hydrochloride, which does not require metals or additives and proceeds at 0–60?°C. The overall transformation involves base mediated intramolecular cyclization of α-N-hydroxyimino-β-oxodithioesters to 4-membered oxazete-4-thione intermediates followed by coupling with chloroalkyl amines via tandem ring cleavage and C?N/C?S bonds formation enabling the construction of thiazolines/thiazines in one-pot. This strategy allows broadening the arsenal of synthetic methods to obtain N,S-heterocycles utilizing substrates prepared according to reported procedures.

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Procduct Name CAS Molecular Formula Supplier Price
2-Chloroethylamine hydrochloride 870-24-6 C2H7Cl2N 602 suppliers $4.00-$1732.50
3-Chloropropylamine hydrochloride 6276-54-6 C3H9Cl2N 443 suppliers $5.00-$7009.70
3-chloropropylamine 14753-26-5 C3H8ClN 19 suppliers Inquiry
2-Chloroethylamine Hydrochloride 1818218-85-7 C10H9NO2 1 suppliers Inquiry

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