Palladium-Catalyzed Oxidative Cyclization for the Synthesis of Indolyl/Pyrrolyl 3-Phosphonates

被引：26

作者：

Mishra, Aniket ^{[1
]}

Deb, Indubhusan ^{[1
]}

机构：

[1] Indian Inst Chem Biol, Organ & Med Chem Div, 4 Raja SC Mullick Rd, Kolkata 700032, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 14期

关键词：

C-H bond activation; imine-enamines; indoles; ketophosphonates; phosphonates; pyrroles; C-H ACTIVATION; N-ARYL ENAMINES; BOND FORMATION; INDOLE-DERIVATIVES; ARYLATION; FUNCTIONALIZATION; PHOSPHORYLATION; INHIBITORS; ANNULATION; AMINATION;

D O I：

10.1002/adsc.201600321

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Imino-/enaminophosphonates derived from amines and diethyl phenacyl phosphonates undergo oxidative cyclization via C-H bond activation catalyzed by palladium chloride to provide a convenient route for the synthesis of substituted indol-3-yl and pyrrol-3-yl phosphonates.

引用

页码：2267 / 2272

页数：6

共 76 条

[11] Copper catalysis in the construction of indole and benzo[b]furan rings [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Goggiamani, Antonella .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) :641-652

[12] Pd(II)-Catalyzed ortho-Arylation of Aryl Phosphates and Aryl Hydrogen Phosphates with Diaryliodonium Triflates [J].

Chan, Li Yan ;

Cheong, Lilian ;

Kim, Sunggak .

ORGANIC LETTERS, 2013, 15 (09) :2186-2189

[13] Rhodium(III)-catalyzed ortho-olefination of aryl phosphonates [J].

Chary, Bathoju Chandra ;

Kim, Sunggak .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (40) :6879-6882

[14] P-Arylation of Dialkyl Phosphites and Secondary Phosphine Oxides with Arynes [J].

Chen, Qian ;

Yan, Xinxing ;

Du, Zhiyun ;

Zhang, Kun ;

Wen, Chunxiao .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01) :276-281

[15] α-Palladation of Imines as Entry to Dehydrogenative Heck Reaction: Aerobic Oxidative Cyclization of N-Allylimines to Pyrroles [J].

Chen, Zhiyuan ;

Lu, Beili ;

Ding, Zhenhua ;

Gao, Ke ;

Yoshikai, Naohiko .

ORGANIC LETTERS, 2013, 15 (08) :1966-1969

[16]

Cho S.H., 2009, Angew. Chem, V121, P9291

[17] Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Lee, S. Yunmi ;

Chang, Sukbok .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) :9127-9130

[18]

d'Ischia M., 2008, Compr. Heterocycl. Chem. III, V3, P353, DOI [10.1016/B978-008044992-0.00304-7, DOI 10.1016/B978-008044992-0.00304-7]

[19] Discovery of phosphonic diamide prodrugs and their use for the oral delivery of a series of fructose 1,6-bisphosphatase inhibitors [J].

Dang, Qun ;

Kasibhatla, Srinivas Rao ;

Jiang, Tao ;

Fan, Kevin ;

Liu, Yan ;

Taplin, Frank ;

Schulz, William ;

Cashion, Daniel K. ;

Reddy, K. Raja ;

van Poelje, Paul D. ;

Fujitaki, James M. ;

Potter, Scott C. ;

Erion, Mark D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (14) :4331-4339

[20] Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes [J].

Debrouwer, Wouter ;

Heugebaert, Thomas S. A. ;

Van Hecke, Kristof ;

Stevens, Christian V. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17) :8232-8241

← 1 2 3 4 5 6 7 8 →