Microwave Promoted One-Pot Synthesis of Some Novel N-Aryl Isoquinoline Derivatives

被引:2
|
作者
Havaldar, Freddy H. [1 ]
Mule, Ganesh B. [1 ]
Dabholkar, Bhushan V. [1 ]
机构
[1] St Xavier Coll, Dept Chem, Nadkarni Sacasa Res Lab, Bombay 400001, Maharashtra, India
关键词
Furo isoquinoline; Pyrano isoquinoline; Microwave; Aza heterocycles; Cyclization; BASE-INDUCED CYCLOADDITION; HOMOPHTHALIC ANHYDRIDES; ANTIFUNGAL ISOCOUMARINS; RECEPTOR ANTAGONISTS; SERIES; CHEMISTRY; ALDEHYDES; DESIGN; CONDENSATION; INHIBITORS;
D O I
10.1002/jhet.1105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Homophthalic anhydride 1 reacts with different aromatic amines to produce N-substituted homophthalimides 2 under microwave irradiation. A rapid microwave-assisted chemical synthesis of condensed 4-substituted furo[2,3-c]isoquinoline-1,5(2H,4H)-diones 3 and 5-substituted-2,3-dihydro-1H-pyrano[2,3-c]isoquinoline-1,6(5H)-diones 4 involving the condensation of a variety of alkanoyl chlorides with 2-arylisoquinoline-1,3-diones 2 in the presence of base and aprotic solvent is described for the first time. By contrast, the facile ring opening reaction of furo[2,3-c]isoquinoline-1,5(2H,4H)-dione 3 with Vilsmeier-Haack reagent under microwave irradiation yielded the - unsaturated carboxyaldehyde 5. This novel and clean one-pot methodology, which is characterized by very short reaction time and easy workup procedure, can be exploited to generate some novel condensed isoquinoline derivatives.
引用
收藏
页码:828 / 837
页数:10
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