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Facile Synthesis of Regioisomeric N‐ Alkyl Substituted 3‐Methylene‐3,4‐dihydroquinoxalin‐2(1 H )‐ones
Author(s) -
Stepanova Ekaterina E.,
Lukmanova Dzhamilya N.,
Kasatkina Svetlana O.,
Dmitriev Maksim V.,
Maslivets Andrey N.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902900
Subject(s) - moiety , methylene , chemistry , regioselectivity , substituent , alkyl , column chromatography , solvent , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
Abstract Facile and convenient synthetic approaches towards pharmaceutically important regioisomeric N ‐alkyl substituted 3‐methylene‐3,4‐dihydroquinoxalin‐2(1 H )‐ones have been developed. Various approaches to the target compounds were tested and compared. Products having bulky N 4 ‐propyl substituent were found to exist in two forms in solutions due to solvent‐dependent rotational processes in 2‐oxoethylidene moiety, which is of interest for construction of optical, electronic, and other functional materials. The proposed procedures proceed in a highly regioselective manner under mild conditions, and the products are isolated without usage of column chromatography.