A Cascade Phosphinoylation/Cyclization/Desulfonylation Process for the Synthesis of 3-Phosphinoylindoles

被引:89
作者
Gao, Yuzhen [1 ,2 ]
Lu, Guozhang [1 ,2 ]
Zhang, Pengbo [1 ,2 ]
Zhang, Liangliang [1 ,2 ]
Tang, Guo [1 ,2 ]
Zhao, Yufen [1 ,2 ,3 ]
机构
[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
[3] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China
关键词
REDUCTIVE CLEAVAGE; AEROBIC OXYPHOSPHORYLATION; CATALYZED CYCLIZATION; PRACTICAL SYNTHESIS; C-P; ALKYNES; FUNCTIONALIZATION; SULFONAMIDES; DERIVATIVES; ARYLATION;
D O I
10.1021/acs.orglett.6b00056
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Phosphinoylindole derivatives play important roles as pharmaceutical drugs and ligands. A new method for the synthesis of 3-phosphinoylindole derivatives has been achieved through silver-mediated cycloaddition between N-Ts-2-alkynylaniline derivatives and H-phosphine oxides. This transformation offers a straightforward route to the formation of the C-P bond, indole ring, and desulfonylation in one step.
引用
收藏
页码:1242 / 1245
页数:4
相关论文
共 43 条
[1]   Phosphono-substituted isoindolines and indoles from 2,3-and 2,4-benzoxazin-1-ones [J].
Abdou, WM ;
Kamel, AA ;
Khidre, MD .
HETEROATOM CHEMISTRY, 2004, 15 (01) :77-84
[2]   Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors [J].
Alexandre, Francois-Rene ;
Amador, Agnes ;
Bot, Stephanie ;
Caillet, Catherine ;
Convard, Thierry ;
Jakubik, Jocelyn ;
Musiu, Chiara ;
Poddesu, Barbara ;
Vargiu, Luana ;
Liuzzi, Michel ;
Roland, Arlene ;
Seifer, Maria ;
Standring, David ;
Storer, Richard ;
Dousson, Cyril B. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) :392-395
[3]  
[Anonymous], 2006, WO PCT Int. Appl., Patent No. 054182
[4]   IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].
Barluenga, J ;
Trincado, M ;
Rubio, E ;
González, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409
[5]  
Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671
[6]   3,3′-bis(diphenylphosphino)-1,1′-disubstituted-2,2′-biindoles:: Easily accessible, electron-rich, chiral diphosphine ligands for homogeneous enantioselective hydrogenation of oxoesters [J].
Benincori, T ;
Piccolo, O ;
Rizzo, S ;
Sannicolò, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8340-8347
[7]   Gold-Catalyzed Oxidative Cyclizations of cis-3-En-1-ynes To Form Cyclopentenone Derivatives [J].
Bhunia, Sabyasachi ;
Ghorpade, Satish ;
Huple, Deepak B. ;
Liu, Rai-Shung .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) :2939-2942
[8]   Reserpine: A challenge for total synthesis of natural products [J].
Chen, FE ;
Huang, J .
CHEMICAL REVIEWS, 2005, 105 (12) :4671-4706
[9]   A one-pot strategy to synthesize β-ketophosphonates: silver/copper catalyzed direct oxyphosphorylation of alkynes with H-phosphonates and oxygen in the air [J].
Chen, Xin ;
Li, Xu ;
Chen, Xiao-Lan ;
Qu, Ling-Bo ;
Chen, Jian-Yu ;
Sun, Kai ;
Liu, Zhi-Dong ;
Bi, Wen-Zhu ;
Xia, Ying-Ya ;
Wu, Hai-Tao ;
Zhao, Yu-Fen .
CHEMICAL COMMUNICATIONS, 2015, 51 (18) :3846-3849
[10]   Silver-Mediated Oxidative C-H/P-H Functionalization: An Efficient Route for the Synthesis of Benzo[b]phosphole Oxides [J].
Chen, Yun-Rong ;
Duan, Wei-Liang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (45) :16754-16757