Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5-b]indoles and Related Heterocycles

Ulises J. Vargas-Cruz; José G. Peralta-Chávez; Misael A. Romero-Reyes; Diego Martínez-Otero; Moisés Romero-Ortega

doi:10.1055/a-2159-1611

Synthesis, Table of Contents

Synthesis 2023; 55(24): 4204-4212
DOI: 10.1055/a-2159-1611

paper

Nitrene Cyclization of 2-(Trichloromethyl)-5-phenylpyrimidines: Application to the Synthesis of 2-(Trichloromethyl)pyrimido[4,5-b]indoles and Related Heterocycles

Ulises J. Vargas-Cruz

^aDepartment of Organic Chemistry, Universidad Autónoma del Estado de México, Toluca, Estado de México, 50180, México

,

José G. Peralta-Chávez

^aDepartment of Organic Chemistry, Universidad Autónoma del Estado de México, Toluca, Estado de México, 50180, México

,

Misael A. Romero-Reyes

^bDepartment of Chemistry, Georgia Gwinnett College, Lawrenceville, GA, 30043, USA

,

Diego Martínez-Otero

^cCentro Conjunto de Investigación en Química Sustentable UAEM-UNAM, Toluca, México

,

Moisés Romero-Ortega ∗

^aDepartment of Organic Chemistry, Universidad Autónoma del Estado de México, Toluca, Estado de México, 50180, México

› Author Affiliations

Abstract

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Abstract

An aromatic C–H nitrene insertion of 2-(trichloromethyl)pyrimidines bearing a phenyl substituent at the C-5 position is described. Treatment of 4-chloro-5-phenyl-2-(trichloromethyl)pyrimidines with sodium azide in DMF or the reflux of 4-azido-5-phenyl-2-(trichloromethyl)pyrimidines in toluene provided 2-(trichloromethyl)pyrimido[4,5-b]indole derivatives in moderate yields. Excellent yields of this heterocyclic system were obtained through the aromatic C–H insertion with the Du Bois catalyst. This is an attractive approach for synthesizing pyrimido[4,5-b]indoles with a trichloromethyl substituent in the pyrimidine moiety.

Key words

nitrene insertion - 5-phenylpyrimidines - pyrimido[4,5-b]indoles - trichloromethylated heterocycles - Du Bois catalyst - intramolecular cyclization

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References

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