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Microwave Promoted One‐Pot Synthesis of Some Novel N ‐Aryl Isoquinoline Derivatives
Author(s) -
Havaldar Freddy H.,
Mule Ganesh B.,
Dabholkar Bhushan V.
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1105
Subject(s) - isoquinoline , chemistry , reagent , microwave irradiation , aryl , organic chemistry , ring (chemistry) , solvent , condensation , combinatorial chemistry , medicinal chemistry , catalysis , alkyl , physics , thermodynamics
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(2 H ,4 H )‐diones 3 and 5‐substituted‐2,3‐dihydro‐1 H ‐pyrano[2,3‐ c ]isoquinoline‐1,6(5 H )‐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(2 H ,4 H )‐dione 3 with Vilsmeier–Haack reagent under microwave irradiation yielded the α‐β 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.