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Synthesis 2019; 51(02): 530-537
DOI: 10.1055/s-0037-1610270
DOI: 10.1055/s-0037-1610270
paper
A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution
The Consejo Nacional de Ciencia y Tecnología (Grant 26659) is gratefully acknowledged and by the fellowship to Michelle Trujillo-Lagunas (EDT, SNI-III).Further Information
Publication History
Received: 16 July 2018
Accepted after revision: 15 August 2018
Publication Date:
11 September 2018 (online)
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 substitutionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610270.
- Supporting Information
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