Title : ( An efficient synthesis of novel spiro[indole-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives via organobase-catalyzed three-component reaction of malononitrile, isatin and heterocyclic-1,3-diones )
Authors: saedehsadat hosseini , Abbas Ali Esmaeili , Amir khojastehnezhad golmakani , Behrouz Notash ,
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Abstract
In this research, firstly, some derivatives of sulfur containing [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one have been synthesized and then they were used for the synthesis of novel derivatives of 6- amino-2,9-dioxo-2-phenyl-9H-spiro[indoline-3,8-pyrano[2,3-d] [1,3,4]thiadiazolo[3,2-a]pyrimidine]-7-carbonitriles via a one-pot three-component condensation reaction of 7-hydroxy-2-phenyl- 5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives, malononitrile and isatin compounds in the presence of DABCO as a organocatalyst and under solvent-free conditions. In this report, a new family of spiro-pyrano-thiadiazolo-pyrimidine derivatives have been synthesized in short reaction times (10–60 min) and good to excellent yields (80–96%). The structures of all synthesized products have been confirmed by IR, 1H NMR, 13C NMR and mass spectrometry, and the structure of one selected product was characterized by single-crystal X-ray diffraction studies as well.
Keywords
, 7-hydroxy-2-phenyl-5H-[1, 3, 4]thiadiazolo[3, 2-a]pyrimidin-5-one; spirooxindole; thiadiazolopyrimidine; organobase-catalyzed; multi-component reactions
@article{paperid:1085452,
author = {Hosseini, Saedehsadat and Esmaeili, Abbas Ali and Khojastehnezhad Golmakani, Amir and Behrouz Notash},
title = {An efficient synthesis of novel spiro[indole-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives via organobase-catalyzed three-component reaction of malononitrile, isatin and heterocyclic-1,3-diones},
journal = {Journal of Sulfur Chemistry},
year = {2021},
volume = {42},
number = {6},
month = {June},
issn = {1741-5993},
pages = {628--644},
numpages = {16},
keywords = {7-hydroxy-2-phenyl-5H-[1;3;4]thiadiazolo[3;2-a]pyrimidin-5-one; spirooxindole; thiadiazolopyrimidine;
organobase-catalyzed; multi-component reactions},
}
%0 Journal Article
%T An efficient synthesis of novel spiro[indole-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives via organobase-catalyzed three-component reaction of malononitrile, isatin and heterocyclic-1,3-diones
%A Hosseini, Saedehsadat
%A Esmaeili, Abbas Ali
%A Khojastehnezhad Golmakani, Amir
%A Behrouz Notash
%J Journal of Sulfur Chemistry
%@ 1741-5993
%D 2021
