Mild and efficient syntheses of diverse isoindolinones from ortho-phthaldehydic acid methylthiomethyl ester

被引:32
作者
Ghosh, Usha [1 ]
Bhattacharyya, Rituparna [1 ]
Keche, Ashish [1 ]
机构
[1] Piramal Life Sci Ltd, Bombay 400063, Maharashtra, India
关键词
Isoindolinones; Reductive amination; Methylthiomethyl ester; Lactamization; CATALYZED CARBONYLATIVE CYCLIZATION; DIELS-ALDER REACTIONS; FUNCTIONALIZED ISOINDOLINONES; ASYMMETRIC-SYNTHESIS; POTENT INHIBITORS; DERIVATIVES; ISOINDOLIN-1-ONES; AUXILIARIES; ALKALOIDS; LIGANDS;
D O I
10.1016/j.tet.2010.01.070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient method for the synthesis of diverse isoindolinones from o-phthaldehydic acid methylthiomethyl ester and aliphatic/aromatic amines has been developed A number of nucleophiles Including a hydride ion were Successfully added to the intermediate Schiff's base providing iso-indolinones. with or Without substitution at 3-position Conditions have also been developed for amines with an integrated nucleophilic group to react in a diverse fashion either to give isoindolinones or tricyclic gamma-lactams as single diastereoisomers in very good yield (C) 2010 Elsevier Ltd All rights reserved
引用
收藏
页码:2148 / 2155
页数:8
相关论文
共 56 条
[1]   ALKALOIDS OF FUMARIA-DENSIFLORA [J].
ABOUDI, AF ;
ALEISAWI, DM ;
SABRI, SS ;
ABUZARGA, MH .
JOURNAL OF NATURAL PRODUCTS, 1986, 49 (02) :370-370
[2]   Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives [J].
Allin, SM ;
Northfield, CJ ;
Page, MI ;
Slawin, AMZ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (11) :1715-1721
[3]   A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives. [J].
Allin, SM ;
Northfield, CJ ;
Page, MI ;
Slawin, AMZ .
TETRAHEDRON LETTERS, 1997, 38 (20) :3627-3630
[4]   TWISTED INTRAMOLECULAR CHARGE-TRANSFER FLUORESCENCE OF AROMATIC AMIDES - CONFORMATION OF THE AMIDE BONDS IN THE EXCITED-STATES [J].
AZUMAYA, I ;
KAGECHIKA, H ;
FUJIWARA, Y ;
ITOH, M ;
YAMAGUCHI, K ;
SHUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :2833-2838
[5]   One-pot synthesis of N-substituted pantolactams from pantolactone [J].
Barrios, I ;
Camps, P ;
Comes-Franchini, M ;
Muñoz-Torrero, D ;
Ricci, A ;
Sánchez, L .
TETRAHEDRON, 2003, 59 (11) :1971-1979
[6]  
BARUM JS, 1989, SYNTHETIC COMMUN, V19, P2283
[7]   Isoindolinone enantiomers having affinity for the dopamine D4 receptor [J].
Belliotti, TR ;
Brink, WA ;
Kesten, SR ;
Rubin, JR ;
Wustrow, DJ ;
Zoski, KT ;
Whetzel, SZ ;
Corbin, AE ;
Pugsley, TA ;
Heffner, TG ;
Wise, LD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (12) :1499-1502
[8]   A chemical switch for inhibitor-sensitive alleles of any protein kinase [J].
Bishop, AC ;
Ubersax, JA ;
Petsch, DT ;
Matheos, DP ;
Gray, NS ;
Blethrow, J ;
Shimizu, E ;
Tsien, JZ ;
Schultz, PG ;
Rose, MD ;
Wood, JL ;
Morgan, DO ;
Shokat, KM .
NATURE, 2000, 407 (6802) :395-401
[9]   THE PHTHALIDEISOQUINOLINE ALKALOIDS [J].
BLASKO, G ;
GULA, DJ ;
SHAMMA, M .
JOURNAL OF NATURAL PRODUCTS, 1982, 45 (02) :105-122
[10]   Synthesis and evaluation in monkey of two sensitive 11C-labeled aryloxyanilide ligands for imaging brain peripheral benzodiazepine receptors in vivo [J].
Briard, Emmanuelle ;
Zoghbi, Sami S. ;
Imaizumi, Masao ;
Gourley, Jonathan P. ;
Shetty, H. Umesha ;
Hong, Jinsoo ;
Cropley, Vanessa ;
Fujita, Masahiro ;
Innis, Robert B. ;
Pike, Victor W. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (01) :17-30