SYNTHESIS OF DIHYDROINDOLES AND TETRAHYDROQUINOLINES BY THE INTRAMOLECULAR DIELS-ALDER REACTION OF N-ALKENYLATED 2-ACYLAMINO-3-FURANCARBONITRILES

被引：1

作者：

Maruoka, Hiroshi ^{[1
]}

Okabe, Fumi ^{[1
]}

Koutake, Yoshimichi ^{[1
]}

Masumoto, Eiichi ^{[1
]}

Fujioka, Toshihiro ^{[1
]}

Yamagata, Kenji ^{[1
]}

机构：

[1] Fukuoka Univ, Fac Pharmaceut Sci, Jonan Ku, Fukuoka 8140180, Japan

来源：

HETEROCYCLES | 2010年 / 81卷 / 06期

关键词：

Dials-Alder Reaction; Cycloaddition; Quinoline; Indole; Furan; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; FARNESYLTRANSFERASE INHIBITORS; ACYL-COA; RING; DERIVATIVES; CYCLIZATION; PALLADIUM; REARRANGEMENT; HETEROCYCLES; AMIDATION;

D O I：

10.3987/COM-10-11936

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to dihydroindoles and tetrahydroquinolines from N-alkenylated 2-acylamino-3-furancarbonitriles via a [4 + 2] cycloaddition reaction is described. Thermal treatment of N-alkenylated 2-acylamino-3-furancarbonitriles 5a-d, 6a-d, 9a-d, and 10a-d, which were prepared from 2-acylamino-3-furancarbonitriles 3a-d and/or 4a-d and 4-bromo-1-butene and/or 5-bromo-1-pentene, caused an intramolecular Diels-Alder reaction to give the corresponding dihydroindole and tetrahydroquinoline derivatives 7a-d, 8a-d, 11a-d, and 12a-d. This method has the advantage of easier work-up procedure.

引用

页码：1467 / 1484

页数：18

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