A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution

Michelle L. Trujillo-Lagunas; Ignacio Medina-Mercado; Ivann Zaragoza-Galicia; Horacio F. Olivo; Moisés Romero-Ortega

doi:10.1055/s-0037-1610270

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(02): 530-537
DOI: 10.1055/s-0037-1610270

paper

A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution

Autor*innen

Michelle L. Trujillo-Lagunas

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

Abstract

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Abstract

A convenient two-step, one-pot synthesis of 4-chloro-2-(trichloromethyl)pyrimidines starting from 2-(trichloromethyl)-1,3-diazabutadienes is described. These nitrogen heterocycles were prepared by a sequential acylation/intramolecular cyclization reaction between 2-(trichloromethyl)-1,3-diazabutadienes and acyl chlorides in the presence of triethylamine followed by treatment with POCl₃. This is the first report for the synthesis of this type of 4-chloro-2-(trichloromethyl)pyrimidine derivatives and serves as a source for a wide variety of other substituted pyrimidines by nucleophilic substitution reactions.

Key words

cycloaddition reaction - tetrachloropyrimidines - 1,3-diazadienes - intramolecular cyclization - nucleophilic substitution

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Referenzen

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