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Fused azole-thiazolines via one-pot cyclization of functionalized N-heterocyclic carbene precursors

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Abstract

A one-pot two-step methodology was exploited to synthesize fused thiazoline-azolium salts via reactions of bromoalkyl-azolium salts with KSCN and NaOH. The synthetic feasibility and versatility was demonstrated by the high yield (>80%) preparation of 13 salts with different backbones, linkers and substituents. Using methylpropionato as an N-protecting group, the resulting salts could be further derivatized to their neutral azole-thiazolines. The reaction sequence proceeds via (i) Br → SCN substitution, (ii) N-heterocyclic carbene formation, (iii) carbene attack of the S atom and CN displacement in the alkyl−S−C[triple bond, length as m-dash]N unit, and (iv) methyl acrylate elimination.

Graphical abstract: Fused azole-thiazolines via one-pot cyclization of functionalized N-heterocyclic carbene precursors

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Article information


Submitted
28 Nov 2019
Accepted
10 Mar 2020
First published
10 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Fused azole-thiazolines via one-pot cyclization of functionalized N-heterocyclic carbene precursors

Q. Teng, C. Singh, Y. Han and H. V. Huynh, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02548K

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