Catalyst free one pot three components synthesis of 2-iminothiazoles from nitroepoxides and thiourea

Elham Badali; Azim Ziyaei Halimehjani; Azizollah Habibi

doi:10.1038/s41598-023-30243-5

Catalyst free one pot three components synthesis of 2-iminothiazoles from nitroepoxides and thiourea

Sci Rep. 2023 Feb 22;13(1):3079. doi: 10.1038/s41598-023-30243-5.

Authors

Elham Badali¹, Azim Ziyaei Halimehjani^{2

3}, Azizollah Habibi¹

Affiliations

¹ Faculty of Chemistry, Kharazmi University, 49 Mofateh St., P. O. Box 15719-14911, Tehran, Iran.
² Faculty of Chemistry, Kharazmi University, 49 Mofateh St., P. O. Box 15719-14911, Tehran, Iran. ziyaei@khu.ac.ir.
³ Department of Chemistry, Sharif University of Technology, P. O. Box 11155-9516, Tehran, Iran. ziyaei@khu.ac.ir.

Abstract

Nitroepoxides were introduced as efficient substrates for the one-pot three-component synthesis of 2-iminothiazoles under catalyst-free conditions. Reaction of amines, isothiocyanates, and nitroepoxides in THF at 10-15 °C afforded corresponding 2-iminothiazoles in high to excellent yields. The reaction proceeds via the in situ formation of thiourea from an amine and an isothiocyanate, followed by nitroepoxide ring opening with the sulfur of thiourea, cyclization reaction, and dehydration cascade. The structures of products were confirmed by IR, NMR, HRMS analyses and X-ray crystallography.