α-Dimethylaminomethylenation-induced Houben-Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones

被引：18

作者：

Kobayashi, Yusuke ^{[1
]}

Nakatani, Terue ^{[1
]}

Tanaka, Rie ^{[1
]}

Okada, Mari ^{[1
]}

Torii, Eri ^{[1
]}

Harayama, Takashi ^{[2
]}

Kimachi, Tetsutaro ^{[1
]}

机构：

[1] Mukogawa Womens Univ, Sch Pharmaceut Sci, Nikshinomiya, Hyogo 6638179, Japan

[2] Tokushima Bunri Univ, Fac Pharmaceut Sci Kagawa Campus, Kagawa 7692193, Japan

来源：

TETRAHEDRON | 2011年 / 67卷 / 19期

关键词：

Electrophilic aromatic substitution; Nitrile; Vilsmeier reagent; Trifluoroacetic anhydride; Triflic anhydride; VILSMEIER REACTION; ARYL KETONES; VERSATILE; QUINOLINES; NITRILES; PHENOL;

D O I：

10.1016/j.tet.2011.03.040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via alpha-dimethylaminomethylenation, which promoted the subsequent Houben-Hoesch-type cyclization. Both alpha-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3457 / 3463

页数：7

共 31 条

[1] SYNTHESIS OF QUINOLINES VIA CYCLIZATION OF 2-CYANO-3-DIMETHYLAMINO-N-(ARYL)ACRYLAMIDES [J].

ADAMS, DR ;

ADAMS, C .

SYNTHETIC COMMUNICATIONS, 1990, 20 (03) :469-475

[2] Synthesis of dixanthones and poly(dixanthone)s by cyclization of 2-aryloxybenzonitriles in trifluoromethanesulfonic acid [J].

Colquhoun, HM ;

Lewis, DF ;

Williams, DJ .

ORGANIC LETTERS, 2001, 3 (15) :2337-2340

[3]

Heaney H., 1991, COMPREHENSIVE ORGANI, V2, P733

[4] A new synthesis of aromatic ketones. I. Representation of some phenol ketones. [J].

Hoesch, K .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1915, 48 :1122-1133

[5] The nuclear condensation of phenols and phenol ethers with nitrils to phenol- and phenol-ether-ketimides and ketones (I) [J].

Houben, J .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1926, 59 :2878-2891

[6] Synthetic strategies to a telomere-targeted pentacyclic heteroaromatic salt [J].

Hutchinson, Ian ;

Stevens, Malcolm F. G. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (01) :114-120

[7] STEREOCHEMISTRY OF NORMAL-METHYLBENZANILIDE AND BENZANILIDE [J].

ITAI, A ;

TORIUMI, Y ;

TOMIOKA, N ;

KAGECHIKA, H ;

AZUMAYA, I ;

SHUDO, K .

TETRAHEDRON LETTERS, 1989, 30 (45) :6177-6180

[8]

Jones G., 1997, ORGANIC REACTIONS, V49, P1

[9]

Jutz C., 1976, ADV ORG CHEM, V9, P225

[10] The construction of novel perylenequinone core via efficient synthesis of versatile ortho-naphthoquinone as a key intermediate [J].

Kim, Beom-Tae ;

Kim, Ho-Seok ;

Moon, Woo Sung ;

Hwang, Ki-Jun .

TETRAHEDRON, 2009, 65 (23) :4625-4628

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