An efficient catalytic method for the Friedlander annulation mediated by peptide coupling agent propylphosphonic anhydride (T3P®)

被引:25
作者
Augustine, John Kallikat [1 ]
Bombrun, Agnes [2 ]
Venkatachaliah, Srinivasa [1 ]
机构
[1] Syngene Int Ltd, Bangalore 560099, Karnataka, India
[2] Merck Serono SA, CH-1202 Geneva, Switzerland
关键词
Friedlander annulation; Propylphosphonic anhydride; Quinolines; Catalytic; Microwave irradiation; PHOSPHONIC ACID ANHYDRIDE; QUINOLINE; QUINAZOLINE; DERIVATIVES; CONVENIENT; PROMOTER; SERIES; MILD;
D O I
10.1016/j.tetlet.2011.10.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have demonstrated the utilization of T3P, a mild and low toxic peptide coupling agent, as a promoter and water scavenger in the Friedlander annulation, and thus introduced a highly efficient catalytic process to access carbocyclic and heterocyclic fused quinolines under microwave irradiation or a conventional heating technique. The reaction conditions are sufficiently mild to tolerate the acid and base sensitive functional groups that can serve as levers for further extension of the quinoline products. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6814 / 6818
页数:5
相关论文
共 42 条
[1]   Propylphosphonic Anhydride (T3P®)-Mediated One-Pot Rearrangement of Carboxylic Acids to Carbamates [J].
Augustine, John Kallikat ;
Bombrun, Agnes ;
Mandal, Ashis Baran ;
Alagarsamy, Padma ;
Atta, Rajendra Nath ;
Selvam, Panneer .
SYNTHESIS-STUTTGART, 2011, (09) :1477-1483
[2]   An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitrites mediated by propylphosphonic anhydride (T3P®) [J].
Augustine, John Kallikat ;
Kumar, Rajesha ;
Bombrun, Agnes ;
Mandal, Ashis Baran .
TETRAHEDRON LETTERS, 2011, 52 (10) :1074-1077
[3]   Propylphosphonic Anhydride (T3P®): A Remarkably Efficient Reagent for the One-Pot Transformation of Aromatic, Heteroaromatic, and Aliphatic Aldehydes to Nitriles [J].
Augustine, John Kallikat ;
Atta, Rajendra Nath ;
Ramappa, Balakrishna Kolathur ;
Boodappa, Chandrakantha .
SYNLETT, 2009, (20) :3378-3382
[4]   Propylphosphonic anhydride (T3P®): an efficient reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles [J].
Augustine, John Kallikat ;
Vairaperumal, Veeramani ;
Narasimhan, Sharmila ;
Alagarsamy, Padma ;
Radhakrishnan, Anbarasi .
TETRAHEDRON, 2009, 65 (48) :9989-9996
[5]   Diversity-Oriented Synthesis of Quinolines via Friedlander Annulation Reaction under Mild Catalytic Conditions [J].
Bose, D. Subhas ;
Idrees, Mohd. ;
Jakka, N. M. ;
Rao, J. Venkateswara .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01) :100-110
[6]   Present trends and future strategy in chemotherapy of malaria [J].
Chauhan, PMS ;
Srivastava, SK .
CURRENT MEDICINAL CHEMISTRY, 2001, 8 (13) :1535-1542
[7]   Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors [J].
Chen, Shuguang ;
Chen, Ran ;
He, Meizi ;
Pang, Ruifang ;
Tan, Zhiwu ;
Yang, Ming .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (05) :1948-1956
[8]   Synthesis and antibacterial evaluation of certain quinolone derivatives [J].
Chen, YL ;
Fang, KC ;
Sheu, JY ;
Hsu, SL ;
Tzeng, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377
[9]  
Cheng C.-C., 1982, ORG REACTIONS, V28
[10]   A one-pot synthesis of imidazo[1,5-a]pyridines [J].
Crawforth, James M. ;
Paoletti, Melissa .
TETRAHEDRON LETTERS, 2009, 50 (34) :4916-4918