3-Hetarylisocoumarins in the synthesis of 1-functionalized 3-hetarylisoquinolines

3-Hetarylisocoumarins in the synthesis of 1-functionalized 3-hetarylisoquinolines

A convenient method was developed for the synthesis of novel isoquinolin-1(2 H )-ones, 1-chloroisoquinolines, and 1-aminoisoquinolines with a heterocyclic substituent in position 3 via a recyclization of 3-hetarylisocoumarins with (NH 4 ) 2 CO 3 . 1-Aminoisoquinolines were efficiently obtained from...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-08, Vol.56 (8), p.1021-1029
Hauptverfasser: Konovalenko, Artem S., Shablykin, Oleh V., Brovarets, Volodymyr S., Shablykina, Olga V., Moskvina, Viktoriia S., Kozytskiy, Andriy V.
Format: Artikel
Sprache:eng
Schlagworte:
Amines
Biological effects
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Morpholine
Organic Chemistry
Pharmacy
Physical Sciences
Science & Technology
Synthesis
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Zusammenfassung:A convenient method was developed for the synthesis of novel isoquinolin-1(2 H )-ones, 1-chloroisoquinolines, and 1-aminoisoquinolines with a heterocyclic substituent in position 3 via a recyclization of 3-hetarylisocoumarins with (NH 4 ) 2 CO 3 . 1-Aminoisoquinolines were efficiently obtained from corresponding 1-chloro-3-hetarylisoquinolines (obtained by interaction of isoquinolin-1(2 H )-ones with POCl 3 ) and cyclic secondary amines (morpholine or 1-methylpiperazine). Literature data and preliminary results of biological assays allow to consider 1-amino-3-hetarylisoquinolines a promising family of anticancer compounds.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02769-3