2-Trifluoromethyl-1,3-diazabutadienes as Useful Intermediates for the Construction of 2-Trifluoromethylpyrimidine Derivatives

Ignacio Medina-Mercado; Ivann Zaragoza-Galicia; Horacio F. Olivo; Moisés Romero-Ortega

doi:10.1055/s-0037-1610444

Synthesis, Table of Contents

Synthesis 2018; 50(20): 4133-4139
DOI: 10.1055/s-0037-1610444

paper

2-Trifluoromethyl-1,3-diazabutadienes as Useful Intermediates for the Construction of 2-Trifluoromethylpyrimidine Derivatives

Ignacio Medina-Mercado

^aDepartamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Toluca, C.P. 50180, México Email: mromeroo@uaemex.mx

,

Ivann Zaragoza-Galicia

^aDepartamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Toluca, C.P. 50180, México Email: mromeroo@uaemex.mx

,

Horacio F. Olivo

^bMedicinal and Natural Products Chemistry, The University of Iowa, Iowa City, IA 52242, USA

,

Moisés Romero-Ortega*

^aDepartamento de Química Orgánica, Facultad de Química, Universidad Autónoma del Estado de México, Toluca, C.P. 50180, México Email: mromeroo@uaemex.mx

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Abstract

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Abstract

A methodology to prepare 2-trifluoromethylpyrimidines has been developed on the basis of a cyclization reaction of 2-trifluoromethyl-1,3-diazabutadienes. These 2-trifluoromethyl-1,3-diazabutadienes were prepared by the condensation of trifluoroacetamidine and amide acetals or with chloromethaniminium salt derived from N,N-dimethylbenzamide with phosphorus oxychloride. The cycloaddition reactions of these 2-trifluoromethyl-1,3-diazabutadienes with DMAD and phenylacetyl chloride provided 2-trifluoromethylpyrimidine derivatives in regular to moderate overall yield.

Key words

trifluoroacetamidine - cycloaddition reaction - 1,3-diazabutadienes - 2-trifluoromethylpyrimidines - trifluoromethyl group

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