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Direct Amination and Synthesis of Fused N ‐Substituted Isothiochromene Derivatives
Author(s) -
AbuHashem Ameen A.,
Zaki Magdi E. A.
Publication year - 2019
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.3466
Subject(s) - chemistry , amination , thiourea , formamide , acetic anhydride , pyridine , yield (engineering) , amide , pyrimidine , organic chemistry , elemental analysis , acetic acid , reductive amination , urea , medicinal chemistry , combinatorial chemistry , stereochemistry , catalysis , materials science , metallurgy
Isothiochromene[3,4‐ d ] pyrimidine derivatives 2 , 3 , and 4a , b were synthesized from the reaction of 3‐amino‐1‐(pyridin‐4‐yl)‐5‐(pyridin‐4‐ylmethylene)‐5,6,7,8‐tetrahydro‐1 H ‐isothiochromene‐4‐carbonitrile 1 with acetic anhydride, formamide, urea, or thiourea in appropriate experimental conditions. Combination of 1 with carbon acid derivatives afforded isothiochromene [3,4‐ b ]pyridine 6 – 8 in good yield. A simple approach for N ‐substituted fused isothiochromene derivatives has been explored. A POCl 3 ‐mediated direct amination of isothiochromene amide 2 with NH 2 ‐heterocycles, secondary amines, and carbohydrazides is described and compared with classical method, yielding 10 – 14 . The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, and spectral data.