Assembly of 3-Substituted Isocoumarins via a Cul-Catalyzed Domino Coupling/Addition/Deacylation Process

被引：91

作者：

Cai, Shangjun ^{[1
]}

Wang, Fei ^{[1
]}

Xi, Chanjuan ^{[1
,2
]}

机构：

[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 05期

基金：

中国国家自然科学基金;

关键词：

BETA-DICARBONYL COMPOUNDS; HYDRANGEAE-DULCIS FOLIUM; ORTHO C-CL; COPPER(I) BENZOATES; INHIBITORY-ACTIVITY; BIOACTIVE FUNCTIONS; EFFICIENT SYNTHESIS; HISTAMINE-RELEASE; HURTLEY REACTION; DIRECT ARYLATION;

D O I：

10.1021/jo2026433

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient strategy for the synthesis of a variety of 3-substituted isocoumarins has been developed. The reaction proceeded from o-halobenzoic acids and 1,3-diketones via a copper(I)-catalyzed domino reaction in DMF under the action of K3PO4 at 90-120 degrees C without a ligand to afford the corresponding 3-substituted isocoumarin derivatives in good to excellent yields. o-Halobenzoic acids could be o-iodobenzoic acid, o-bromobenzoic acid, and o-chlorobenzoic acid derivatives. 1,3-Diketones could be alkyl- and aryl-substituted 1,3-diketones.

引用

页码：2331 / 2336

页数：6

共 72 条

[1] THE HURTLEY REACTION .2. NOVEL COMPLEXES OF DISUBSTITUTED ACETYLENES WITH COPPER(I) BENZOATES HAVING A REACTIVE ORTHO C-CL OR C-BR BOND - X-RAY STRUCTURAL CHARACTERIZATION OF TETRAKIS(2-CHLOROBENZOATO)BIS(DIETHYL ACETYLENEDICARBOXYLATE)TETRACOPPER(I)
AALTEN, HL
VANKOTEN, G
RIETHORST, E
STAM, CH
[J]. INORGANIC CHEMISTRY, 1989, 28 (22) : 4140 - 4146
[2] THE HURTLEY REACTION .1. SYNTHESIS AND CHARACTERIZATION OF COPPER(I) BENZOATES CONTAINING REACTIVE ORTHO C-CL, C-BR BONDS AND THEIR REACTIVITY TOWARD ORGANOCOPPER(I) COMPOUNDS - CRYSTAL-STRUCTURE OF A THERMALLY STABLE TRINUCLEAR HETERO COPPER(I) CLUSTER, BIS(BENZOATO)MESITYLTRICOPPER(I)
AALTEN, HL
VANKOTEN, G
GOUBITZ, K
STAM, CH
[J]. ORGANOMETALLICS, 1989, 8 (10) : 2293 - 2299
[3] CONDENSATION OF BETA-DICARBONYL COMPOUNDS WITH HALOGENOPYRIDINECARBOXYLIC ACIDS - CONVENIENT SYNTHESIS OF SOME NAPHTHYRIDINE DERIVATIVES
AMES, DE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (05): : 705 - &
[4] Angelis M.D., 2005, Bioorganic and Medicinal Chemistry, V13, P6529
[5] METAL-IONS AND COMPLEXES IN ORGANIC REACTIONS .20. COPPER-CATALYZED REACTIONS OF AROMATIC BROMO-CARBOXYLATES WITH CARBANIONS, GIVING OXO-ACIDS, ISOCOUMARINS, AND RELATED PRODUCTS
BACON, RGR
MURRAY, JCF
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (13): : 1267 - 1272
[6] THE BIOSYNTHESIS OF CITRININ BY PENICILLIUM-CITRINUM
BARBER, J
CARTER, RH
GARSON, MJ
STAUNTON, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09): : 2577 - 2583
[7] STUDIES ON SRN1 REACTIONS .6. SYNTHESIS OF 3-METHYL DERIVATIVES OF THE ALKALOIDS THALACTAMINE, DORYANINE, AND 6,7-DIMETHOXY-N-METHYL-1(2H)-ISOQUINOLONE
BEUGELMANS, R
GINSBURG, H
BOISCHOUSSY, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (05): : 1149 - 1152
[8] Oxidation of 3-arylisochromans by dimethyldioxirane. An easy route to substituted 3-arylisocoumarins.
Bovicelli, P
Lupattelli, P
Crescenzi, B
Sanetti, A
Bernini, R
[J]. TETRAHEDRON, 1999, 55 (51) : 14719 - 14728
[9] STUDY OF COPPER-CATALYZED DIRECT ARYLATION OF BETA-DICARBONYL COMPOUNDS WITH 2-BROMOBENZOIC ACIDS
BRUGGINK, A
MCKILLOP, A
[J]. TETRAHEDRON, 1975, 31 (20) : 2607 - 2619
[10] Green heterocycle synthesis, isochromenones and artemidin
Bryson, TA
Stewart, JJ
Gibson, JM
Thomas, PS
Berch, JK
[J]. GREEN CHEMISTRY, 2003, 5 (02) : 174 - 176

← 1 2 3 4 5 6 7 8 →