On triazoles XLIV [1]. synthesis of new ring systems containing imidazo[2′,1′:3,4] [1,2,4] triazolo [1,5-a]pyrimidine and imidazo[1′,2′:2,3][1,2,4]triazolo[1,5-a]pyrimidine skeleton
✍ Scribed by Gábor Berecz; József Reiter; Gyula Argay; Alajos Kálmán
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2002
- Tongue
- English
- Weight
- 85 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0022-152X
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Dedicated to Dr. János Császár on the occasion of his 70^th^ birthday
Ring transformation of 2‐cyanoimido‐3‐methyl‐1,3‐oxazolidine (10) yielded 5‐amino‐3‐[N‐(2‐hydrox‐yethyl)‐N‐methyl]amino‐1__H__‐1,2,4‐triazole (6) that was ring closed with different β‐keto esters to 2‐[N‐(2‐hydroxyethyl)‐N‐methyl]amino‐1,2,4‐triazolo[1,5‐a]pyrimidinones (4). Cyclisation of derivatives 4 led to imidazo[2′,1′:3,4][1,2,4]triazolo[1,5‐a]pyrimidines (2) and imidazo[1′,2′:2,3][1,2,4]triazolo[1,5‐a]pyrim‐idines (3) representing 10 novel ring systems. Besides spectroscopical evidence of structure of derivatives 2 and 3 X‐ray diffraction analysis of derivative 2b was also performed.
📜 SIMILAR VOLUMES
Hydrazonoyl bromides 1a-c react with 5-amino-3phenyl-1H-pyrazole, 5-amino-1H-1,2,4-triazole, 2aminopyridine, 2-aminopyrimidine, and 2-aminobenzimidazole to afford the corresponding imidazo[1,2-b]pyrazoles 10, imidazo[1,2-b]-1,2,4-triazoles 11, imidazo[1,2-a]pyridines 16, imidazo[1,2-a]pyrimidines 17
## Abstract Some new 1,2,3‐triazolo[4,5‐__e__]‐1,2,4‐triazolo[3,4‐__c__]pyrimidmes were prepared starting from the corresponding 1,2,3‐triazolo[4,5‐__d__]pyrimidines __via__ the formation of the 1,2,4‐triazole ring. Thus suitable hydrazino derivatives 6 were condensed with triethyl orthoformate, tr
## Abstract Derivatives of the new ring system pyrrolo[3,4‐__e__][1,2,3] triazolo[1,5‐__a__]pyrimidine **6** were prepared in high yields in one step by reaction of 3‐azidopyrrole **3** and substituted acetonitriles. Compound **6b** rearranged, upon heating in dimethyl sulfoxide in the presence of
## Abstract The 7‐chloro‐3‐(2‐chlorobenzyl)‐ and 7‐chloro‐3‐(2‐fluorobenzyl)‐1,2,3‐triazolo[4,5‐__d__]pyrimidines (**1** and **4**), by nucleophilic replacement with some hydrazides, gave the corresponding 7‐hydrazidoderivatives (**2a‐e** and **5a‐e**). These, by heating in Dowtherm, underwent an i