Phenylboronic acid as an efficient and convenient catalyst for a three-component synthesis of tetrahydrobenzo[b]pyrans

被引：93

作者：

Nemouchi, Sara ^{[1
]}

Boulcina, Raouf ^{[1
]}

Carboni, Bertrand ^{[2
]}

Debache, Abdelmadjid ^{[1
]}

机构：

[1] Univ Mentouri Constantine, Lab Prod Nat Origine Vegetale & Synth Organ, Dept Chim, Fac Sci Exactes, Constantine 25000, Algeria

[2] Univ Rennes 1, CNRS, UMR 6226, F-35042 Rennes, France

来源：

COMPTES RENDUS CHIMIE | 2012年 / 15卷 / 05期

关键词：

Multi-component reaction; One-pot synthesis; Tetrahydrobenzo[b]pyrans; Phenylboronic acid; ONE-POT SYNTHESIS; TETRABUTYLAMMONIUM BROMIDE; DERIVATIVES; MILD; CYCLOADDITIONS; IRRADIATION;

D O I：

10.1016/j.crci.2012.01.003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Phenylboronic acid, a non-toxic compound, is used as catalyst for an efficient, rapid, and one-pot three-component synthesis of tetrahydrobenzo[b]pyrans in good to excellent yields. This new procedure has the advantages of operational simplicity, shorter reaction time, higher yields and minimum pollution of the environment. (C) 2012 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

引用

页码：394 / 397

页数：4

共 40 条

[1]

ABDELLATIF FF, 1995, J CHEM RES-S, P178

[2] Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media [J].

Abdolmohammadi, Shahrzad ;

Balalaie, Saeed .

TETRAHEDRON LETTERS, 2007, 48 (18) :3299-3303

[3] Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature [J].

Al-Zoubi, Raed M. ;

Marion, Olivier ;

Hall, Dennis G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2876-2879

[4]

Andreani L.L., 1960, BOLL CHIM FARM, V99, P583

[5]

[Anonymous], 1995, Compr. Heterocycl. Chem. II, DOI DOI 10.1016/B978-008096518-5.00112-X

[6] SYNTHESIS OF CYCLOBUTENES BY THE NOVEL PHOTOCHEMICAL RING CONTRACTION OF 4-SUBSTITUTED 2-AMINO-3,5-DICYANO-6-PHENYL-4H-PYRANS [J].

ARMESTO, D ;

HORSPOOL, WM ;

MARTIN, N ;

RAMOS, A ;

SEOANE, C .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3069-3072

[7] Asymmetric direct amide synthesis by kinetic amine resolution:: A chiral bifunctional aminoboronic acid catalyzed reaction between a racemic amine and an achiral carboxylic acid [J].

Arnold, Kenny ;

Davies, Bryan ;

Herault, Damien ;

Whiting, Andrew .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (14) :2673-2676

[8] Tetra-methyl ammonium hydroxide:: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media [J].

Balalaie, Saeed ;

Sheikh-Ahmadi, Masoumeh ;

Bararjanian, Morteza .

CATALYSIS COMMUNICATIONS, 2007, 8 (11) :1724-1728

[9] SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2-OXO-(2H) 1-BENZOPYRAN-3-CARBOXAMIDE DERIVATIVES [J].

BONSIGNORE, L ;

LOY, G ;

SECCI, D ;

CALIGNANO, A .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) :517-520

[10] The thermal and boron-catalysed direct amide formation reactions: mechanistically understudied yet important processes [J].

Charville, Hayley ;

Jackson, David ;

Hodges, George ;

Whiting, Andrew .

CHEMICAL COMMUNICATIONS, 2010, 46 (11) :1813-1823

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