Baylis-Hillman acetates in carbocyclic synthesis: a convenient protocol for synthesis of densely substituted indenes

被引：9

作者：

Basavaiah, Deevi ^{[1
]}

Reddy, Bhavanam Sekhara ^{[1
]}

Lingam, Harathi ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

TETRAHEDRON | 2013年 / 69卷 / 08期

关键词：

Baylis-Hillman reaction; Friedel-Crafts reaction; Chemo selectivity; Indene derivatives; Keto-diesters; FRIEDEL-CRAFTS ALKYLATION; FACILE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; ALLYLIC ALKYLATION; SOLID CATALYSTS; MICHAEL-ALDOL; ADDUCTS; CYCLIZATION; ACID;

D O I：

10.1016/j.tet.2012.12.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and facile strategy for synthesis of densely substituted indenes have been developed from Baylis-Hillman acetates in a two step protocol, that is, (1) via treatment with DABCO and then reaction with alkyl 3-oxobutanoates in the presence of K2CO3 (2) followed by the intramolecular Friedel Crafts cyclization of the resulting keto-diesters using titanium tetrachloride. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：1994 / 2003

页数：10

共 78 条

[1] A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel-Crafts reactions [J].

Angeli, Marco ;

Bandini, Marco ;

Garelli, Andrea ;

Piccinelli, Fabio ;

Tommasi, Simona ;

Umani-Ronchi, Achille .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) :3291-3296

[2] SN2′ versus SN2 Reactivity: Control of Regioselectivity in Conversions of Baylis-Hillman Adducts [J].

Baidya, Mahiuddin ;

Remennikov, Grygoriy Y. ;

Mayer, Peter ;

Mayr, Herbert .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (04) :1365-1371

[3] Solid-State Melt Reaction for the Domino Process: Highly Efficient Synthesis of Fused Tetracyclic Chromenopyran Pyrimidinediones Using Baylis-Hillman Derivatives [J].

Bakthadoss, Manickam ;

Sivakumar, Govindan ;

Kannan, Damodharan .

ORGANIC LETTERS, 2009, 11 (19) :4466-4469

[4]

Basavaiah D, 1996, SYNLETT, P393

[5] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

[6]

Basavaiah D, 2001, SYNTHESIS-STUTTGART, P919

[7] FIRST ENANTIOSELECTIVE SYNTHESIS OF MIKANECIC ACID VIA DIELS-ALDER CYCLOADDITION MEDIATED CONSTRUCTION OF CHIRAL VINYLIC QUATERNARY CENTER [J].

BASAVAIAH, D ;

PANDIARAJU, S ;

SARMA, PKS .

TETRAHEDRON LETTERS, 1994, 35 (24) :4227-4230

[8] One-pot inter- and intramolecular Friedel-Crafts reactions in Baylis-Hillman chemistry:: a novel facile synthesis of (E)-2-arylideneindan-1-ones [J].

Basavaiah, D ;

Reddy, RM .

TETRAHEDRON LETTERS, 2001, 42 (16) :3025-3027

[9] Baylis-Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes [J].

Basavaiah, D ;

Kumaragurubaran, N ;

Sharada, DS .

TETRAHEDRON LETTERS, 2001, 42 (01) :85-87

[10] The Friedel-Crafts reaction of the Baylis-Hillman adducts [J].

Basavaiah, D ;

Krishnamacharyulu, M ;

Hyma, RS ;

Pandiaraju, S .

TETRAHEDRON LETTERS, 1997, 38 (12) :2141-2144

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