Volume 31, Issue 23
Preparative Organic Chemistry
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ChemInform Abstract: A Versatile One-Pot Synthesis of 1,3-Substituted Guanidines from Carbamoyl Isothiocyanates.

Brian R. Linton

Brian R. Linton

Dep. Chem., Univ. Pittsburgh, Pittsburgh, PA 15260, USA

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Andrew J. Carr

Andrew J. Carr

Dep. Chem., Univ. Pittsburgh, Pittsburgh, PA 15260, USA

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Brendan P. Orner

Brendan P. Orner

Dep. Chem., Univ. Pittsburgh, Pittsburgh, PA 15260, USA

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Andrew D. Hamilton

Andrew D. Hamilton

Dep. Chem., Univ. Pittsburgh, Pittsburgh, PA 15260, USA

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First published: 08 June 2010

Abstract

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ChemInform Abstract

Carbamoyl isothiocyanates are ideal starting materials for the two-step one-pot synthesis of multisubstituted guanidines from two separate amines. In the first step, carbamates of type (I) or (VII) are coupled with aliphatic or aromatic amines to give thioureas in excellent yields which are coupled in the second step with another amine to afford the desired guanidines. Thioureas (IIIc) and (IIId) as well as (VIIIc) and (VIIId) failed to form guanidines in detectable yields. Multisubstituted guanidine (XII) is also obtained by this method.

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