Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives

Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide...

Full description

Bibliographic Details
Main Authors: MAGDI E. A. ZAKI, OSAMA I. ABD EL-SALAM, SAMIRA A. SWELAM
Format: Article
Language:English
Published: Serbian Chemical Society 1999-11-01
Series:Journal of the Serbian Chemical Society
Subjects:
Online Access:http://www.shd.org.yu/HtDocs/SHD/Vol64/No11-Pdf/V64-no11-02.zip
_version_ 1818232158141022208
author MAGDI E. A. ZAKI
OSAMA I. ABD EL-SALAM
SAMIRA A. SWELAM
author_facet MAGDI E. A. ZAKI
OSAMA I. ABD EL-SALAM
SAMIRA A. SWELAM
author_sort MAGDI E. A. ZAKI
collection DOAJ
description Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with hydrazine hydrate to afford the monohydrazino derivative 15. Reaction of 15, with formic acid and nitrous acid afforded pyrazolo[4,3-e]triazolo[1,5-c]pyrimidine (16) and pyrazolo[4,3-e]tetrazolo-[1,5-c]pyrimidine (17) derivatives, respectively. The structures of products 3-17 were identified in light of their elemental analyses and spectra data.
first_indexed 2024-12-12T11:01:50Z
format Article
id doaj.art-7b33e27aeb3943cda051ba09fa8ac0f8
institution Directory Open Access Journal
issn 0352-5139
language English
last_indexed 2024-12-12T11:01:50Z
publishDate 1999-11-01
publisher Serbian Chemical Society
record_format Article
series Journal of the Serbian Chemical Society
spelling doaj.art-7b33e27aeb3943cda051ba09fa8ac0f82022-12-22T00:26:30ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391999-11-016411655662Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivativesMAGDI E. A. ZAKIOSAMA I. ABD EL-SALAMSAMIRA A. SWELAMReaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with hydrazine hydrate to afford the monohydrazino derivative 15. Reaction of 15, with formic acid and nitrous acid afforded pyrazolo[4,3-e]triazolo[1,5-c]pyrimidine (16) and pyrazolo[4,3-e]tetrazolo-[1,5-c]pyrimidine (17) derivatives, respectively. The structures of products 3-17 were identified in light of their elemental analyses and spectra data.http://www.shd.org.yu/HtDocs/SHD/Vol64/No11-Pdf/V64-no11-02.zippyrazolo[34-d]pyrimidinem-thiazinerearragnementtriazolo[15-c]-pyrimidinetetrazolo[15-c]pyrimidine
spellingShingle MAGDI E. A. ZAKI
OSAMA I. ABD EL-SALAM
SAMIRA A. SWELAM
Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives
Journal of the Serbian Chemical Society
pyrazolo[3
4-d]pyrimidine
m-thiazine
rearragnement
triazolo[1
5-c]-pyrimidine
tetrazolo[1
5-c]pyrimidine
title Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives
title_full Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives
title_fullStr Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives
title_full_unstemmed Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives
title_short Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives
title_sort synthesis of some pyrazolo 3 4 d pyrimidines and their fused triazole and tetrazole derivatives
topic pyrazolo[3
4-d]pyrimidine
m-thiazine
rearragnement
triazolo[1
5-c]-pyrimidine
tetrazolo[1
5-c]pyrimidine
url http://www.shd.org.yu/HtDocs/SHD/Vol64/No11-Pdf/V64-no11-02.zip
work_keys_str_mv AT magdieazaki synthesisofsomepyrazolo34dpyrimidinesandtheirfusedtriazoleandtetrazolederivatives
AT osamaiabdelsalam synthesisofsomepyrazolo34dpyrimidinesandtheirfusedtriazoleandtetrazolederivatives
AT samiraaswelam synthesisofsomepyrazolo34dpyrimidinesandtheirfusedtriazoleandtetrazolederivatives