Rhodium(III)-Catalysed Carbenoid C(sp2)-H Functionalisation of Aniline Substrates with α-Diazo Esters: Formation of Oxindoles and Characterisation/Utility of an Intermediate-Like Rhodacycle

被引：31

作者：

Allu, Srinivasarao ^{[1
]}

Ravi, Manjula ^{[1
]}

Swamy, K. C. Kumara ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 34期

关键词：

C-H activation; Rhodium; Homogeneous catalysis; Nucleobases; Nitrogen heterocycles; Nucleosides; C-H ACTIVATION; REVERSE-TRANSCRIPTASE INHIBITORS; BOND FUNCTIONALIZATION; DIRECTING GROUP; METAL CARBENE; RH(III)-CATALYZED SYNTHESIS; N-OXIDES; BIOLOGICAL EVALUATIONS; FACILE SYNTHESIS; DERIVATIVES;

D O I：

10.1002/ejoc.201600968

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Rh-III-catalysed reaction of 2-anilinopyridines with sulfonylated alpha-diazo esters under mild conditions gave oxindole derivatives, while an analogous reaction of anilinopyrimidine precursors using alpha-diazo esters led to the ortho- alkylation products. The carbenoid coupling reaction was successfully extended to 6-anilinopurine/purine nucleosides, and the ortho-alkylated 6-anilinopurines could be obtained in excellent yields. Proof of the involvement of an Rh-C-bonded species comes from the characterisation of an intermediate-like rhodacycle (which is also an active catalyst) by single-crystal X-ray crystallography.

引用

页码：5697 / 5705

页数：9