Cyclization of o-Alkynylisocyanobenzenes with 1,3-Dicarbonyl Compounds

被引：1

作者：

La-ongthong, Kannika ^{[1
,2
]}

Sawekteeratana, Natthapat ^{[1
,2
]}

Klaysuk, Jasarin ^{[1
,2
]}

Soorukram, Darunee ^{[1
,2
]}

Leowanawat, Pawaret ^{[1
,2
]}

Reutrakul, Vichai ^{[1
,2
]}

Krobthong, Sucheewin ^{[3
]}

Wongtrakoongate, Patompon ^{[1
,4
]}

Kuhakarn, Chutima ^{[1
,2
]}

机构：

[1] Mahidol Univ, Fac Sci, Dept Chem, Rama 6 Rd, Bangkok 10400, Thailand

[2] Mahidol Univ, Fac Sci, Ctr Excellence Innovat Chem PERCH CIC, Bangkok 10400, Thailand

[3] Mahidol Univ, Fac Sci, Ctr Neurosci & Cent Instrument Facil, Rama 6 Rd, Bangkok 10400, Thailand

[4] Mahidol Univ, Ctr Neurosci, Fac Sci, Rama 6 Rd, Bangkok 10400, Thailand

来源：

SYNLETT | 2022年 / 33卷 / 14期

关键词：

alkynylisocyanobenzenes; isonitriles; dicarbonyl compounds; Bronsted bases; quinolines; METAL-FREE SYNTHESIS; ISOCYANIDE INSERTION; RADICAL CYCLIZATION; HETEROAROMATICS QUINOLINES; CASCADE; DERIVATIVES; 2-ARYLQUINOLINES; FRAGMENTATIONS; ANNULATION; NITRILES;

D O I：

10.1055/a-1784-2513

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and convenient reaction of o-alkynylisocyanobenzenes with various active-methylene compounds, including 1,3-diesters, 1,3-diketones, beta-keto esters, and beta-keto amides, under Bronsted basic conditions, has been developed. Diethyl malonate reacted smoothly with a collection of o-alkynylisocyanobenzenes to provide the corresponding 2-quinolin-2-yl malonates in excellent yields. Acetylacetone gave a mixture of quinolin-4-yl and quinolin-2-yl derivatives. Acetoacetate esters and acetoacetyl amide derivative initially gave 2-quinolin-2-yl adducts that underwent partial deacetylation under the reaction conditions.

引用

页码：1411 / 1418

页数：8

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