Indium trichloride catalyzed efficient one-pot synthesis of highly substituted furans

被引：19

作者：

Dey, Sumit ^{[1
]}

Nandi, Debkumar ^{[1
]}

Pradhan, Prasun K. ^{[1
]}

Giri, Venkatachalam Sesha ^{[1
]}

Jaisankar, Parasuraman ^{[1
]}

机构：

[1] Indian Inst Chem Biol, Unit CSIR, Dept Med Chem, Kolkata 700032, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 14期

关键词：

indium trichloride; furans; cyclization; dehydration;

D O I：

10.1016/j.tetlet.2007.02.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot synthesis of the substituted furans 3 could be achieved in good yields by reacting but-2-ene-1,4-diones 1 with acetoacetates 2 in the presence of a catalytic amount of InCl3 (20 mol %) using i-PrOH as solvent at 80-90 degrees C for 4-8 h. InCl3 was observed to give the optimum results among the various Lewis acids examined. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2573 / 2575

页数：3

共 33 条

[1] FURANNULATION STRATEGY FOR SYNTHESIS OF THE NATURALLY-OCCURRING FUSED 3-METHYLFURANS - EFFICIENT SYNTHESIS OF EVODONE AND MENTHOFURAN AND REGIOSELECTIVE SYNTHESIS OF MATURONE VIA A LEWIS-ACID CATALYZED DIELS-ALDER REACTION - SOME COMMENTS FOR ITS MECHANISTIC ASPECTS
ASO, M
OJIDA, A
YANG, G
CHA, OJ
OSAWA, E
KANEMATSU, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 3960 - 3968
[2] Imino Diels-Alder reactions catalyzed by indium trichloride (InCl3). Facile synthesis of quinoline and phenanthridinone derivatives.
Babu, G
Perumal, PT
[J]. TETRAHEDRON LETTERS, 1997, 38 (28) : 5025 - 5026
[3] Indium tribromide:: a highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones
Bandini, M
Cozzi, PG
Melchiorre, P
Umani-Ronchi, A
[J]. TETRAHEDRON LETTERS, 2001, 42 (16) : 3041 - 3043
[4] Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones
Bandini, M
Cozzi, PG
Giacomini, M
Melchiorre, P
Selva, S
Umani-Ronchi, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) : 3700 - 3704
[5] Indium tribromide-catalyzed chemoselective dithioacetalization of aldehydes in non-aqueous and aqueous media
Ceschi, MA
Felix, LD
Peppe, C
[J]. TETRAHEDRON LETTERS, 2000, 41 (50) : 9695 - 9699
[6] SYNTHESIS OF A SOLUBLE NONACENETRIQUINONE VIA A BISISOBENZOFURAN
CHRISTOPFEL, WC
MILLER, LL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) : 4169 - 4175
[7] LOPHOTOXIN - A NOVEL NEUROMUSCULAR TOXIN FROM PACIFIC SEA WHIPS OF THE GENUS LOPHOGORGIA
FENICAL, W
OKUDA, RK
BANDURRAGA, MM
CULVER, P
JACOBS, RS
[J]. SCIENCE, 1981, 212 (4502) : 1512 - 1514
[8] PREPARATION OF 1,4-DIKETONES AND THEIR REACTIONS WITH BIS(TRIALKYLTIN) OR BIS(TRIPHENYLTIN) SULFIDE BORON-TRICHLORIDE
FREEMAN, F
KIM, DSHL
RODRIGUEZ, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) : 1722 - 1727
[9] Hashmi A.S.K., 2000, ANGEW CHEM, V112, P2382, DOI DOI 10.1002/CCTC.200900237
[10] Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P2285, DOI 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO

← 1 2 3 4 →