Synthesis of isoquinoline-3-carboxylates and benzocyclobutanes via reaction of 2-amidoacrylate esters with arynes

被引：29

作者：

Blackburn, Tom ^{[1
]}

Ramtohul, Yeeman K. ^{[1
]}

机构：

[1] Merck Frosst Canada & Co Inc, Dept Med Chem, Merck Frosst Ctr Therapeut Res, Kirkland, PQ H9H 3L1, Canada

来源：

SYNLETT | 2008年 / 08期

关键词：

arynes; isoquinoline heterocycles; benzocyclobutanes; annulations; 2-amidoacrylate esters;

D O I：

10.1055/s-2008-1072723

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

A mild and general method for the synthesis of a variety of 2-substituted isoquinoline 3-carboxylates and benzocyclobutanes from the reaction of 2-amidoacrylate esters with arynes has been developed.

引用

页码：1159 / 1164

页数：6

共 18 条

[1]

New synthesis of 7-azabicyclo[2.2.1]heptane-1-carboxylic acid [J].

Avenoza, A ;

Cativiela, C ;

Busto, JH ;

Fernández-Recio, MA ;

Peregrina, JM ;

Rodríguez, F .

TETRAHEDRON, 2001, 57 (03) :545-548

[2]

Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins [J].

Chen, C ;

Zhu, YF ;

Liu, XJ ;

Lu, ZX ;

Xie, Q ;

Ling, N .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (23) :4001-4010

[3]

Orthogonal synthesis of indolines and isoquinolines via aryne annulation [J].

Gilmore, Christopher D. ;

Allan, Kevin M. ;

Stoltz, Brian M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) :1558-+

[4]

FLUORIDE-INDUCED 1,2-ELIMINATION OF ORTHO-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS [J].

HIMESHIMA, Y ;

SONODA, T ;

KOBAYASHI, H .

CHEMISTRY LETTERS, 1983, (08) :1211-1214

[5]

Reaction of arynes, N-heteroaromatics and nitriles [J].

Jeganmohan, Masilamani ;

Cheng, Chien-Hong .

CHEMICAL COMMUNICATIONS, 2006, (23) :2454-2456

[6]

Kessar S.V., 1991, COMPREHENSIVE ORGANI, V4, P483

[7]

Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids [J].

Liu, ZJ ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08) :3198-3209

[8]

Insertion of arynes into σ bonds [J].

Pena, Diego ;

Perez, Dolores ;

Guitian, Enrique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (22) :3579-3581

[9]

Direct C-arylation of β-enamino esters and ketones with arynes [J].

Ramtohul, Yeeman K. ;

Chartrand, Anik .

ORGANIC LETTERS, 2007, 9 (06) :1029-1032

[10]

Arylnaphthalene lignans through Pd-catalyzed [2+2+2] cocyclization of arynes and diynes: Total synthesis of taiwanins C and E [J].

Sato, Y ;

Tamura, T ;

Mori, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) :2436-2440

← 1 2 →