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

[21] Oxidative Cleavage of C-C Bonds in Lignin
Subbotina, Elena
Rukkijakan, Thanya
Marquez Medina, Maria Dolores
Yu, Xiaowen
Johnsson, Mats
Samec, Joseph S. M.
SYNLETT, 2022, 33 (04) : A44 - A46
[22] Oxidative cleavage of C-C bonds in lignin
Subbotina, Elena
Rukkijakan, Thanya
Marquez-Medina, M. Dolores
Yu, Xiaowen
Johnsson, Mats
Samec, Joseph S. M.
NATURE CHEMISTRY, 2021, 13 (11) : 1118 - +
[23] New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds
Sangster, Jack J.
Marshall, James R.
Turner, Nicholas J.
Mangas-Sanchez, Juan
CHEMBIOCHEM, 2022, 23 (06)
[24] Selective Cleavage and Tunable Functionalization of the C-C/C-N Bonds of N-Arylpiperidines Promoted by tBuONO
He, Yan
Zheng, Zhi
Liu, Yajie
Qiao, Jiajie
Zhang, Xinying
Fan, Xuesen
ORGANIC LETTERS, 2019, 21 (06) : 1676 - 1680
[25] Iodine-Induced Regioselective C-C and C-N Bonds Formation of N-Protected Indoles
Li, Ying-Xiu
Ji, Ke-Gong
Wang, Hai-Xi
Ali, Shaukat
Liang, Yong-Min
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02): : 744 - 747
[26] Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation
Yip, KT
Yang, M
Law, KL
Zhu, NY
Yang, D
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) : 3130 - 3131
[27] Copper-Catalyzed Synthesis of 2-Aminocarbazoles through Cascade C-C and C-N Bond Formation and Aromatization
Liu, Xinlei
Huang, Jiangkun
Xu, Huibei
Zhang, Dandan
Sun, Qiu
He, Ling
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (05) : 900 - 906
[28] Transition-metal-free Oxidative Coupling Reactions for the Formation of C-C and C-N Bonds Mediated by TEMPO and its Derivatives
Murarka, Sandip
Wertz, Sebastian
Studer, Armido
CHIMIA, 2012, 66 (06) : 413 - 417
[29] Cleaner, safer synthesis of C-N bonds
Crow, James Mitchell
CHEMISTRY WORLD, 2007, 4 (02): : 22 - 22
[30] Formation of C-C and C-N bonds through primary alcohol oxidation catalyzed by ruthenium(II) POCOP pincer complexes
Roque-Ramires, Manuel A.
Restrepo-Acevedo, Andres C.
Cuenu-Cabezas, Fernando
Le Lagadec, Ronan
APPLIED ORGANOMETALLIC CHEMISTRY, 2024, 38 (11)

← 1 2 3 4 5 →