Guanidine derivativesQ 0660 DOI: 10.1002/chin.201212072

N-Bromosuccinimide Promoted One-Pot Synthesis of Guanidine: Scope and Mechanism. — A one-pot procedure for the preparation of guanidine derivatives from an olefin, cyanamide, amine and NBS is developed. Cyclic or cis-disubstituted olefins lead to the open-chain products [cf. (IV)]. Other substrates yield the cyclic guanidines. Open-chain guanidines can be converted to the cyclic ones without isolation of the in-termediates by heating the reaction mixture [cf. (XX)]. Guanidine (XIII) is obtained from the trifluoroacetamide, while no reaction takes place when trichloroacetamide is used. Key intermediate for the synthesis of the rTRPVI inhibitor is prepared using the method [cf. (XVIII)]. — (ZHOU, L.; CHEN, J.; ZHOU, J.; YEUNG*, Y.-Y.; Org. Lett. 13 (2011) 21, 5804-5807, http://dx.doi.org/10.1021/ol202402y ; Dep. Chem., Natl. Univ. Singapore, Singapore 117543, Singapore; Eng.) — R. Steudel

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ChemInform 2012, 43, issue 12 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ChemInform 2012, 43, issue 12 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim