A solvent-free synthesis of coumarins via Pechmann condensation using heterogeneous catalyst

被引：92

作者：

Maheswara, Muchchintala ^{[1
]}

Siddaiah, Vidavalur ^{[1
]}

Damu, Guri Lakishmi Vasantha ^{[1
]}

Rao, Yeffa Koteswara ^{[1
]}

Rao, Chunduti Venkata ^{[1
]}

机构：

[1] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2006年 / 255卷 / 1-2期

关键词：

phenols; ethyl acetoacetate; methyl acetoacetate; cournarins; HClO4 center dot SiO2; recyclable heterogeneous catalyst; solvent-free conditions;

D O I：

10.1016/j.molcata.2006.03.051

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Substituted coumarins are synthesized from phenols and ethyl acetoacetate or methyl acetoacetate via Pechmann condensation using heterogeneous recyclable catalyst (HClO4 (.) SiO2) under solvent-free conditions. This method is simple, cost effective, requires short reaction times and benefits from the elimination of production of acidic waste streams generated with conventional acid catalyst to give good yields. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：49 / 52

页数：4

共 32 条

[1]

AHMAD ZS, 1937, P INDIAN ACAD SCI A, V5, P277

[2]

AHMAD ZS, 1937, CHEM ABSTR 5785, V31

[3]

[Anonymous], 1914, CHEM BER-RECL, DOI DOI 10.1002/CBER.191404702131

[4]

Appel H, 1935, J CHEM SOC, P1031

[5] Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the knoevenagel synthesis of coumarin-3-carboxylic acids [J].

Bigi, F ;

Chesini, L ;

Maggi, R ;

Sartori, G .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1033-1035

[6] Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines [J].

Chakraborti, AK ;

Gulhane, R .

CHEMICAL COMMUNICATIONS, 2003, (15) :1896-1897

[7] An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition [J].

Cravotto, G ;

Nano, GM ;

Palmisano, G ;

Tagliapietra, S .

TETRAHEDRON-ASYMMETRY, 2001, 12 (05) :707-709

[8] DALBERGIA SPECIES .6. OCCURRENCE OF MELANNEIN IN GENUS DALBERGIA [J].

DONNELLY, BJ ;

DONNELLY, DM ;

OSULLIVAN, AM .

TETRAHEDRON, 1968, 24 (06) :2617-+

[9] A novel class of inhibitors for steroid 5α-reductase:: Synthesis and evaluation of umbelliferone derivatives [J].

Fan, GJ ;

Mar, W ;

Park, MK ;

Choi, EW ;

Kim, K ;

Kim, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (17) :2361-2363

[10] Microwave acceleration of the Pechmann reaction on graphite/montmorillonite K10:: application to the preparation of 4-substituted 7-aminocoumarins [J].

Frère, S ;

Thiéry, V ;

Besson, T .

TETRAHEDRON LETTERS, 2001, 42 (15) :2791-2794

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