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

被引：0

作者：

Vargas-Cruz, Ulises J. ^{[1
]}

Peralta-Chavez, Jose G. ^{[1
]}

Romero-Reyes, Misael A. ^{[2
]}

Martinez-Otero, Diego ^{[3
]}

Romero-Ortega, Moises ^{[1
]}

机构：

[1] Univ Autonoma Estado Mexico, Dept Organ Chem, Toluca 50180, Estado De Mexic, Mexico

[2] Georgia Gwinnett Coll, Dept Chem, Lawrenceville, GA 30043 USA

[3] Ctr Conjunto Invest Quim Sustentable UAEM UNAM, Toluca, Mexico

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 24期

关键词：

nitrene insertion; 5-phenylpyrimidines; pyrimido[4,5-b ]indoles; trichloromethylated heterocycles; Du Bois catalyst; intramolecular cyclization; DIELS-ALDER REACTIONS; C-H AMINATION; POTENT; INHIBITORS; ACCESS; RING; PHOTOCHEMISTRY; DECOMPOSITION; NUCLEOSIDE; INSERTION;

D O I：

10.1055/a-2159-1611

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4204 / 4212

页数：9

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