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：30

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

共 86 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds [J].

Ai, Wen ;

Yang, Xueyan ;

Wu, Yunxiang ;

Wang, Xuan ;

Li, Yuanchao ;

Yang, Yaxi ;

Zhou, Bing .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) :17653-17657

[3] Palladium-catalysed ortho-acylation of 6-anilinopurines/purine nucleosides via C-H activation [J].

Allu, Srinivasarao ;

Swamy, K. C. Kumara .

RSC ADVANCES, 2015, 5 (112) :92045-92054

[4] Ruthenium-Catalyzed Oxidative Annulation of 6-Anilinopurines with Alkynes via C-H Activation: Synthesis of Indole-Substituted Purines/Purine Nucleosides [J].

Allu, Srinivasarao ;

Swamy, K. C. Kumara .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (12) :2665-2680

[5] Ruthenium-Catalyzed Synthesis of lsoquinolones with 8-Aminoquinoline as a Bidentate Directing Group in C-H Functionalization [J].

Allu, Srinivasarao ;

Swamy, K. C. Kumara .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :3963-3972

[6]

[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANIE.201201666

[7]

[Anonymous], ANGEW CHEM, DOI DOI 10.1002/ANGE.201309650

[8]

[Anonymous], 1997, SHELX 97 PROGRAM CRY

[9]

[Anonymous], 2013, Angew. Chem, DOI DOI 10.1002/ANGE.201301451

[10]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]

← 1 2 3 4 5 6 7 8 9 →