A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine

Hitesh B. Jalani; V. Sudarsanam; Kamala K. Vasu

doi:10.1055/s-0032-1317504

Synthesis, Table of Contents

Synthesis 2012; 44(21): 3378-3386
DOI: 10.1055/s-0032-1317504

paper

A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine

Hitesh B. Jalani

Department of Medicinal Chemistry, B.V. Patel Pharmaceutical Education and Research Development (PERD) Centre, Sarkhej-Gandhinagar Highway, Thaltej, Ahmedabad 380 054, Gujarat, India Fax: +91(79)27450449 Email: kamkva@gmail.com

,

V. Sudarsanam

Department of Medicinal Chemistry, B.V. Patel Pharmaceutical Education and Research Development (PERD) Centre, Sarkhej-Gandhinagar Highway, Thaltej, Ahmedabad 380 054, Gujarat, India Fax: +91(79)27450449 Email: kamkva@gmail.com

,

Kamala K. Vasu*

Department of Medicinal Chemistry, B.V. Patel Pharmaceutical Education and Research Development (PERD) Centre, Sarkhej-Gandhinagar Highway, Thaltej, Ahmedabad 380 054, Gujarat, India Fax: +91(79)27450449 Email: kamkva@gmail.com

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Abstract

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In loving memory of my grandfather, S. J. Jalani

Abstract

An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino- or guanidinothiourea to give chemoselectively N-hydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exo-trig cyclization.

Key words

1,2,4-oxadiazol-3-amine - metallic thiophile - chemoselectivity - N-hydroxyguanidine

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References

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