Synthesis of Indolizines through Oxidative Linkage of C-C and C-N Bonds from 2-Pyridylacetates

被引：44

作者：

Mohan, Darapaneni Chandra ^{[1
]}

Ravi, Chitrakar ^{[1
]}

Pappula, Venkatanarayana ^{[1
]}

Adimurthy, Subbarayappa ^{[1
]}

机构：

[1] CSIR Cent Salt & Marine Chem Res Inst, Acad Sci & Innovat Res, Bhavnagar 364002, Gujarat, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 13期

关键词：

ONE-POT; MULTICOMPONENT SYNTHESIS; CYCLIZATION; KETONES; FUNCTIONALIZATION; DERIVATIVES; ANNULATION; ALKYNES; IODINE; 2-ALKYLAZAARENES;

D O I：

10.1021/acs.joc.5b00477

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of indolizine-1-carboxylates through the Ortoleva-King reaction of 2-pyridylacetate followed by the Aldol condensation under mild reaction conditions has been described. This protocol is compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the regioselective formation of benzoyl-substituted indolizines through Michael addition followed by C-N bond formation, which are difficult to prepare by previous methods in a single step.

引用

页码：6846 / 6855

页数：10

共 50 条

[31] Greener nickel-catalyzed cross-couplings to forge C-C and C-N bonds
Garg, Neil
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
[32] Lewis Acid-Catalyzed Generation of C-C and C-N Bonds on π-Deficient Heterocyclic Substrates
Staderini, Matteo
Bolognesi, Maria Laura
Carlos Menendez, J.
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (01) : 185 - 195
[33] Iron-Catalyzed Reduction of CO2 into Methylene: Formation of C-N, C-O, and C-C Bonds
Jin, Guanghua
Werncke, C. Gunnar
Escudie, Yannick
Sabo-Etienne, Sylviane
Bontemps, Sebastien
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (30) : 9563 - 9566
[34] Formation and evolution of C-C, C-O, C=O and C-N bonds in chemical reactions of prebiotic interest
Arias, Alejandro
Gomez, Sara
Rojas-Valencia, Natalia
Nunez-Zarur, Francisco
Cappelli, Chiara
Murillo-Lopez, Juliana A.
Restrepo, Albeiro
RSC ADVANCES, 2022, 12 (44) : 28804 - 28817
[35] Synthesis of 2,2'-Bipyridines through Catalytic C-C Bond Formations from C-H Bonds
Hagui, Wided
Periasamy, Kiruthika
Soule, Jean-Francois
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (39) : 5388 - 5402
[36] Copper(II)-Catalyzed Aerobic Oxidative Synthesis of Substituted 1,2,3-and 1,2,4-Triazoles from Bisarylhydrazones via C-H Functionalization/C-C/N-N/C-N Bonds Formation
Guru, Murali Mohan
Punniyamurthy, Tharmalingam
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11): : 5063 - 5073
[37] Developments towards synthesis of N-heterocycles from amidines via C-N/C-C bond formation
Guo, Wei
Zhao, Mingming
Tan, Wen
Zheng, Lvyin
Tao, Kailiang
Fan, Xiaolin
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2120 - 2141
[38] Forging C-C Bonds through Intramolecular Oxidative Coupling of Organoborates - An Overview
Didier, Dorian
SYNTHESIS-STUTTGART, 2023, 55 (02): : 232 - 239
[39] Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C-C and C-N bonds
Yan, Kelu
Yang, Daoshan
Wei, Wei
Li, Guoqing
Sun, Mingyang
Zhang, Qingyun
Tian, Laijin
Wang, Hua
RSC ADVANCES, 2015, 5 (121): : 100102 - 100105
[40] Divergent synthesis of α-functionalized amides through selective N-O/C-C or N-O/C-C/C-N cleavage of aza-cyclobutanone oxime esters
Liu, Hua-Wei
Wang, Dian-Liang
Jiang, Nan-Quan
Li, Hai-Yan
Cai, Zhong-Jian
Ji, Shun-Jun
CHEMICAL COMMUNICATIONS, 2021, 57 (75) : 9618 - 9621

← 1 2 3 4 5 →