A multicomponent synthesis of gem-(β-dicarbonyl)arylmethanes

被引：27

作者：

Appendino, Giovanni ^{[1
]}

Cicione, Lavinia ^{[1
]}

Minassi, Alberto ^{[1
]}

机构：

[1] Univ Piemonte Orientale, Dipartimento Sci Chim Alimentari Farmaceut & Farm, I-28100 Novara, Italy

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 40期

关键词：

Multicomponent reactions; 4-Hydroxycoumarin; Indole; Dehydroacetic acid; COUMARIN DERIVATIVES; ALPHA-PYRONE; CHEMISTRY; MICROPHYLLUM; ARZANOL;

D O I：

10.1016/j.tetlet.2009.05.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of aldehydes with beta-dicarbonyls and electron-rich aromatics was investigated to generate in a multicomponent fashion crossed adducts of biological relevance. 4-Hydroxycoumarin, triacetic acid lactone, indole, and a selection of aliphatic and aromatic aldehydes representative of various electronic and steric conditions were employed. The reaction showed a surprising dependence on the solvent, with 1:1 chloroform-water giving the best yield of heterodimeric adducts. The mechanistic rationale for the formation of hetero- rather than homodimeric adducts is discussed. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5559 / 5561

页数：3

共 10 条

[1] THE CHEMISTRY OF COUMARIN DERIVATIVES .5. UNUSUAL COURSE OF THE REACTION OF 4-HYDROXYCOUMARIN AND ALIPHATIC-ALDEHYDES [J].

APPENDINO, G ;

CRAVOTTO, G ;

NANO, GM ;

PALMISANO, G ;

ANNUNZIATA, R .

HELVETICA CHIMICA ACTA, 1993, 76 (03) :1194-1202

[2] THE CHEMISTRY OF COUMARIN DERIVATIVES .3. SYNTHESIS OF 3-ALKYL-4-HYDROXYCOUMARINS BY REDUCTIVE FRAGMENTATION OF 3,3'-ALKYLIDENE-4,4'-DIHYDROXYBIS[COUMARINS] [J].

APPENDINO, G ;

CRAVOTTO, G ;

TAGLIAPIETRA, S ;

FERRARO, S ;

NANO, GM ;

PALMISANO, G .

HELVETICA CHIMICA ACTA, 1991, 74 (07) :1451-1458

[3] Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol α-pyrone from Helichrysum italicum ssp microphyllum [J].

Appendino, Giovanni ;

Ottino, Michela ;

Marquez, Nieves ;

Bianchi, Federica ;

Giana, Anna ;

Ballero, Mauro ;

Sterner, Olov ;

Fiebich, Bernd L. ;

Munoz, Eduardo .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (04) :608-612

[4]

HANSCHUTZ R, 1909, LIEBIGS ANN CHEM, V367, P169

[5] HARD SOFT ACIDS BASES (HSAB) PRINCIPLE AND ORGANIC-CHEMISTRY [J].

HO, TL .

CHEMICAL REVIEWS, 1975, 75 (01) :1-20

[6] Evaluation of the antioxidant and cytotoxic activity of arzanol, a prenylated α-pyrone-phloroglucinol etherodimer from Helichrysum italicum subsp microphyllum [J].

Rosa, Antonella ;

Deiana, Monica ;

Atzeri, Angela ;

Corona, Giulia ;

Incani, Alessandra ;

Melis, M. Paola ;

Appendino, Giovanni ;

Dessi, M. Assunta .

CHEMICO-BIOLOGICAL INTERACTIONS, 2007, 165 (02) :117-126

[7] Cancer chemotherapy with indole-3-carbinol, bis(3′-indolyl)methane and synthetic analogs [J].

Safe, Stephen ;

Papineni, Sabitha ;

Chintharlapalli, Sudhakar .

CANCER LETTERS, 2008, 269 (02) :326-338

[8]

Stahmann MA, 1941, J BIOL CHEM, V138, P513

[9]

VELEZHEVA VS, 1973, ZH ORG KHIM+, V9, P185

[10] Identification of indole derivatives as self-growth inhibitors of Symbiobacterium thermophilum, a unique bacterium whose growth depends on coculture with a Bacillus sp. [J].

Wdtsuji, Tomo-o ;

Yamada, Shinya ;

Yamabe, Tomoya ;

Watanabe, Yuka ;

Kato, Taira ;

Saito, Takao ;

Ueda, Kenji ;

Beppu, Teruhiko .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2007, 73 (19) :6159-6165

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