Premium
Synthesis of substituted 3‐(5‐amino‐[1,3,4]thiadiazol‐2‐yl)‐2 H ‐pyrano[2,3‐ c ]pyridin‐2‐ones
Author(s) -
Zhuravel' Irina O.,
Kovalenko Sergiy M.,
Ivachtchenko Alexandre V.,
Chernykh Valentin P.,
Shinkarenko Pavlo E.
Publication year - 2004
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.5570410407
Subject(s) - chemistry , pyridine , knoevenagel condensation , cyanoacetamide , carboxamide , hydrochloride , stereochemistry , medicinal chemistry , intermolecular force , condensation , organic chemistry , molecule , catalysis , physics , thermodynamics
An efficient two‐step synthesis of novel 3‐(5‐amino‐[1,3,4]thiadiazol‐2‐yl)‐2 H ‐pyrano[2,3‐ c ]pyridine‐2‐ones was developed. In the first step, a new 2 H ‐pyrano[2,3‐ c ]pyridine‐3‐carboxamide 5 was prepared by Knoevenagel condensation of pyridoxal hydrochloride with cyanoacetamide. In the second step, the reaction of carboxamide 5 with a series of N 4 ‐substituted thiosemicarbazides yielded a library of 35 dis crete compounds 8 {1–35} in high yields. The intermolecular recyclization mechanism leading to these products is discussed.