Silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a highly efficient, heterogeneous and recyclable silica-supported ionic liquid catalyst for the synthesis of benzo[b]pyran, bis(benzo[b]pyran) and spiro-pyran derivatives

被引：101

作者：

Hasaninejad, Alireza ^{[1
]}

Golzar, Nooshin ^{[1
]}

Beyrati, Maryam ^{[1
]}

Zare, Abdolkarim ^{[2
]}

Doroodmand, Mohammad Mahdi ^{[3
]}

机构：

[1] Persian Gulf Univ, Fac Sci, Dept Chem, Bushehr 75169, Iran

[2] Payame Noor Univ, Dept Chem, Tehran 193954697, Iran

[3] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2013年 / 372卷

关键词：

Silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl; 4H-benzo[b]pyran; Spiro-pyrans; Silica-supported catalyst; Malono derivatives; ONE-POT SYNTHESIS; SOLVENT-FREE; SALICYLIC ALDEHYDES; X-RAY; DBU; SPIROOXINDOLES; REAGENTS; KETONES; FACILE; ROUTE;

D O I：

10.1016/j.molcata.2013.02.022

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：

The reaction of 3-chloropropyl silica (SilprCl) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dry acetone affords silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (SB-DBU)Cl as a new silica-supported ionic liquid catalyst. Afterward, (SB-DBU)Cl is used for the efficient synthesis of 4H-benzo[b]pyran derivatives via the one-pot, three-component reaction of carbonyl compounds (cyclohexane-1,3-dione, 5,5-dimethylcyclohexane-1,3-dione or 3-methyl-1-phenyl-2-pyrazolin-5-one) with aromatic aldehydes and alkylmalonates. Moreover, some novel bis(benzo[b]pyran)s and a broad range of structurally diverse spiro-pyrans containing oxindole and/or quinoxaline moiety in their structures are synthesized using (SB-DBU)Cl. The catalyst is recycled and reused fifteen times with unchanged yield. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：137 / 150

页数：14

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