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3‐Oxobutanamides in Heterocyclic Synthesis, Synthesis Approaches for new Pyridines, Pyrimidines and their Fused Derivatives
Author(s) -
Hussein Abdel Haleem M.,
ElAdasy AbuBakr A.,
Khames Ahmed A.,
Atalla Ahmed A.,
AbdelRady Mohamed
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601424
Subject(s) - malononitrile , yield (engineering) , chemistry , pyridine , derivative (finance) , reagent , ethyl cyanoacetate , condensation , nucleophile , condensation reaction , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , catalysis , physics , economics , financial economics , metallurgy , thermodynamics
Condensation of 3‐oxobutanamide derivative 1 with DMF‐DMA afforded the thiazolopyrimidines 4 , pyridine derivative 7 and naphthyridines 12 depending on the different reaction conditions. Condensation of 1 with triethylorthoformate afforded ethoxymethylene derivative 3 . The ethoxymethylenes 3 reacted with different nucleophilic reagents to yield 14 , 15 , 20 and 23–25 respectively. Also, it reacted with malononitrile and ethyl cyanoacetate to give pyridine derivatives 28 a,b . Finally, the ethoxymethylenes 3 reacted with β‐naphthol to yield the benzoquinoline derivative 34 .