Synthesis of Various Derivatives of a Novel Heterocyclic System of Tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine
Author:
, , , , ,Year
: 2019
Abstract: 1,2,3-Triazole has become one of the most important heterocycles in current chemistry research,
due to its important industrial, agrochemical and pharmaceutical applications, especially
in biological science, material chemistry, and medicinal chemistry [1]. Additionally, the
chemistry of the tetrazole ring is gaining increasing attention due to its importance in a variety
of synthetic and industrial processes and excellent properties as a metabolically stable isosteric
replacement for the carboxylic acid moiety and as a cis-peptide bond mimetic [2]. Tetrazoles
have also been used as precursors to other heterocycles and in high energy compounds
[3]. In the present work, initially the reaction of 2,4-dichloro-6-methylpyrimidin-5-
amine (1) with different primary amines in refluxing i-PrOH gave the corresponding secamino
derivatives which were consequently treated with NaNO2/HCl solution to yield quantitatively
the corresponding diazo derivatives of 5-chloro-3-alkyl-7-methyl-3H-
[1,2,3]triazolo[4,5-d]pyrimidine (2a-e). Further reaction of compounds (2a-e) with NaN3 in
EtOH was resulted in various derivatives of novel heterocyclic system of tetrazolo[1,5-
a][1,2,3]triazolo[4,5-d]pyrimidine (3a-e) that are in equilibrium with azide forms.
due to its important industrial, agrochemical and pharmaceutical applications, especially
in biological science, material chemistry, and medicinal chemistry [1]. Additionally, the
chemistry of the tetrazole ring is gaining increasing attention due to its importance in a variety
of synthetic and industrial processes and excellent properties as a metabolically stable isosteric
replacement for the carboxylic acid moiety and as a cis-peptide bond mimetic [2]. Tetrazoles
have also been used as precursors to other heterocycles and in high energy compounds
[3]. In the present work, initially the reaction of 2,4-dichloro-6-methylpyrimidin-5-
amine (1) with different primary amines in refluxing i-PrOH gave the corresponding secamino
derivatives which were consequently treated with NaNO2/HCl solution to yield quantitatively
the corresponding diazo derivatives of 5-chloro-3-alkyl-7-methyl-3H-
[1,2,3]triazolo[4,5-d]pyrimidine (2a-e). Further reaction of compounds (2a-e) with NaN3 in
EtOH was resulted in various derivatives of novel heterocyclic system of tetrazolo[1,5-
a][1,2,3]triazolo[4,5-d]pyrimidine (3a-e) that are in equilibrium with azide forms.
Keyword(s): Tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine
Collections
:
-
Statistics
Synthesis of Various Derivatives of a Novel Heterocyclic System of Tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine
Show full item record
| contributor author | نیلوفر دیندار فولادلو | en |
| contributor author | صدیقه شیخی محمره | en |
| contributor author | علی شیری | en |
| contributor author | niloofar dindar fouladloo | fa |
| contributor author | Seddigheh Sheikhi-Mohammareh | fa |
| contributor author | Ali Shiri | fa |
| date accessioned | 2020-06-06T14:30:27Z | |
| date available | 2020-06-06T14:30:27Z | |
| date copyright | 3/12/2019 | |
| date issued | 2019 | |
| identifier uri | http://libsearch.um.ac.ir:80/fum/handle/fum/3399660?locale-attribute=en | |
| description abstract | 1,2,3-Triazole has become one of the most important heterocycles in current chemistry research, due to its important industrial, agrochemical and pharmaceutical applications, especially in biological science, material chemistry, and medicinal chemistry [1]. Additionally, the chemistry of the tetrazole ring is gaining increasing attention due to its importance in a variety of synthetic and industrial processes and excellent properties as a metabolically stable isosteric replacement for the carboxylic acid moiety and as a cis-peptide bond mimetic [2]. Tetrazoles have also been used as precursors to other heterocycles and in high energy compounds [3]. In the present work, initially the reaction of 2,4-dichloro-6-methylpyrimidin-5- amine (1) with different primary amines in refluxing i-PrOH gave the corresponding secamino derivatives which were consequently treated with NaNO2/HCl solution to yield quantitatively the corresponding diazo derivatives of 5-chloro-3-alkyl-7-methyl-3H- [1,2,3]triazolo[4,5-d]pyrimidine (2a-e). Further reaction of compounds (2a-e) with NaN3 in EtOH was resulted in various derivatives of novel heterocyclic system of tetrazolo[1,5- a][1,2,3]triazolo[4,5-d]pyrimidine (3a-e) that are in equilibrium with azide forms. | en |
| language | English | |
| title | Synthesis of Various Derivatives of a Novel Heterocyclic System of Tetrazolo[1,5-a][1,2,3]triazolo[4,5-d]pyrimidine | en |
| type | Conference Paper | |
| contenttype | External Fulltext | |
| subject keywords | Tetrazolo[1 | en |
| subject keywords | 5-a][1 | en |
| subject keywords | 2 | en |
| subject keywords | 3]triazolo[4 | en |
| subject keywords | 5-d]pyrimidine | en |
| identifier link | https://profdoc.um.ac.ir/paper-abstract-1073456.html | |
| identifier articleid | 1073456 |