Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine

被引：5

作者：

Barrera, Edson ^{[1
]}

Israel Hernandez-Benitez, R. ^{[1
]}

Gonzalez-Gonzalez, Carlos A. ^{[2
]}

Escalante, Carlos H. ^{[1
]}

Fuentes-Benites, Aydee ^{[2
]}

Gonzalez-Romero, Carlos ^{[2
]}

Becerra-Martinez, Elvia ^{[3
]}

Delgado, Francisco ^{[1
]}

Tamariz, Joaquin ^{[1
]}

机构：

[1] Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Dept Quim Organ, Prol Carpio & Plan Ayala S-N, Mexico City 11340, DF, Mexico

[2] Univ Autonoma Estado Mexico, Dept Quim Organ, Fac Quim, Paseo Tollocan S-N, Toluca 50000, Estado De Mexic, Mexico

[3] Inst Politecn Nacl, Ctr Nanociencias & Micro & Nanotecnol CNMN, Unidad Profes Adolfo Lopez Mateos, Av Luis Enrique Erro S-N, Mexico City 07738, DF, Mexico

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 24期

关键词：

Ellipticine; Methylcarbazoles; Microwave chemistry; 4-Oxazolin-2-ones; Palladium; PALLADIUM-CATALYZED SYNTHESIS; VILSMEIER-HAACK REACTION; AUSTRALE MULL-ARGOV; CARBAZOLE ALKALOIDS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; DERIVATIVES; 9-METHOXYELLIPTICINE; INTERMEDIATE; ARYLATION;

D O I：

10.1002/ejoc.202200364

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New and efficient strategies for the conversion of 4-oxazolin-2-ones into 1-methyl and 1,4-dimethyl 3-formylcarbazoles are herein described. Highly convergent cascade and one-pot processes afforded the corresponding diarylamines, as in situ formed synthetic intermediates or final products in high overall yields. Special attention was given to the synthesis of methylated carbazoles by reacting 4,5-dimethyl-4-oxazolin-2-ones with enones under microwave irradiation. The carbazole scaffold was provided by the palladium(II)-catalyzed double C-H activation to generate oxidative cyclization of diarylamines. This methodology allowed for formal total syntheses of four naturally occurring pyrido[4,3-b]carbazole alkaloids ellipticine, 9-methoxyellipticine, olivacine, and 9-methoxyolivacine.

引用

页数：7

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