Microwave assisted copper-free Sonogashira coupling/5-exo-dig cycloisomerization domino reaction: access to 3-(phenylmethylene)isoindolin-1-ones and related heterocycles

被引：76

作者：

Hellal, Malik

Cuny, Gregory D. ^{[1
]}

机构：

[1] Brigham & Womens Hosp, Harvard NeuroDiscovery Ctr, Lab Drug Discovery Neurodegenerat, Cambridge, MA 02139 USA

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 42期

关键词：

Isoindoline; Domino reaction; Cycloisomerization; Sonogashira coupling; Microwave; PALLADIUM-CATALYZED REACTION; O-IODOBENZOIC ACID; ONE-POT SYNTHESIS; INTRAMOLECULAR CYCLIZATION; SUBSTITUTED; 3-METHYLENEISOINDOLIN-1-ONES; STEREOSELECTIVE-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; 4+2 CYCLOADDITION; ACETYLENIC ACIDS;

D O I：

10.1016/j.tetlet.2011.08.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient microwave assisted one-pot synthesis of substituted 3-(phenylmethylene)isoindolin-1-ones is reported via a copper-free Sonogashira coupling and a regioselective 5-exo-dig cycloisomerization. This domino reaction was also extended to other related heterocycles. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5508 / 5511

页数：4

共 73 条

[1]

ARCADI A, 1992, TETRAHEDRON LETT, V33, P3915

[2] PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES AND VINYL ARYL HALIDES WITH 4-ALKYNOIC ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-DELTA-VINYL ARYL-GAMMA-METHYLENE-GAMMA-BUTYROLACTONES [J].

ARCADI, A ;

BURINI, A ;

CACCHI, S ;

DELMASTRO, M ;

MARINELLI, F ;

PIETRONI, BR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :976-982

[3] Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].

Asao, N ;

Kasahara, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506

[4] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].

Asao, N ;

Nogami, T ;

Lee, S ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925

[5] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[6] Formation of spiro indane derivatives from hydroxy lactams derived from N-(1-phenylethyl)-phthalimide and -pyridine-2,3-dicarboximide [J].

Bahajaj, AA ;

Vernon, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (10) :1041-1046

[7] Pd-Cu catalyzed heterocyclization during Sonogashira coupling:: synthesis of 2-benzylimidazo[1,2-a]pyridine [J].

Bakherad, Mohammad ;

Nasr-Isfahani, Hossein ;

Keivanloo, Ali ;

Doostmohammadi, Nesa .

TETRAHEDRON LETTERS, 2008, 49 (23) :3819-3822

[8] A remarkable accelerating effect of Ag-salt on intramolecular cyclization of o-(1-alkynyl)benzenesulfonamides [J].

Barange, Deepak Kumar ;

Nishad, T. C. ;

Swamy, N. Kumara ;

Bandameedi, Venkanna ;

Kumar, Dinesh ;

Sreekanth, Bukkapattanam R. ;

Vyas, K. ;

Pal, Manojit .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8547-8550

[9] Regioselective construction of six-membered fused heterocyclic rings via Pd/C-mediated C-C coupling followed by iodocyclization strategy:: a new entry to 2H-1,2-benzothiazine-1,1-dioxides [J].

Barange, Deepak Kumar ;

Batchu, Venkateswara Rao ;

Gorja, Dhillirao ;

Pattabiraman, Vijaya Raghavan ;

Tatini, Lakshmi Kumar ;

Babu, J. Moses ;

Pal, Manojit .

TETRAHEDRON, 2007, 63 (08) :1775-1789

[10] THE PHTHALIDEISOQUINOLINE ALKALOIDS [J].

BLASKO, G ;

GULA, DJ ;

SHAMMA, M .

JOURNAL OF NATURAL PRODUCTS, 1982, 45 (02) :105-122

← 1 2 3 4 5 6 7 8 →