Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols

被引：3

作者：

Yin, Haiting ^{[1
]}

Wu, Yunjun ^{[1
]}

Gu, Xiaoxia ^{[1
]}

Feng, Zhijun ^{[1
]}

Wang, Meifang ^{[1
,2
]}

Feng, Dexiang ^{[1
]}

Wang, Ming ^{[1
]}

Cheng, Ziyang ^{[1
]}

Wang, Shaoyin ^{[1
,2
]}

机构：

[1] Wannam Med Coll, Dept Chem, Inst Synth & Applicat Med Mat, Chunhui Sci Res Interest Grp, Wuhu 241002, Peoples R China

[2] Anhui Med Univ, Key Lab Antiinflammatory & Immune Med, Minist Educ, Hefei 230032, Peoples R China

来源：

RSC ADVANCES | 2022年 / 12卷 / 33期

基金：

中国国家自然科学基金;

关键词：

TETRAHYDRO-BETA-CARBOLINES; ONE-POT SYNTHESIS; FACILE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; MILD APPROACH; ALKALOIDS; QUINOLINE; CYCLOISOMERIZATION; FUROQUINOLINONES;

D O I：

10.1039/d2ra03416f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two acid-catalyzed tandem reactions between 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols are described. Depending mainly on the propargylic alcohol used, these tandem reactions proceed via either a Friedel-Crafts-type allenylation followed by 6-endo-dig cyclization sequence to form pyrano[3,2-c]quinolones or a Friedel-Crafts-type alkylation and 5-exo-dig ring closure sequence to afford furo[3,2-c]quinolones in moderate-to-high yields. The pyrano[3,2-c]quinolones products could be further transformed to tetracyclic 4,9-dihydro-5H-cyclopenta[lmn]phenanthridin-5-one derivatives.

引用

页码：21066 / 21078

页数：13

共 74 条

[1] DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].