Switchable pathways of multicomponent heterocyclizations of 5-amino-1,2,4-triazoles with salicylaldehydes and pyruvic acid

• Yana I. Sakhno,
• Oleksander V. Buravov,
• Kostyantyn Yu. Yurkov,
• Anastasia Yu. Andryushchenko,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2030–2035, doi:10.3762/bjoc.21.158

• multicomponent reaction of the same starting materials led to the formation of only tetrahydrotriazolopyrimidine derivatives. Keywords: 5-amino-1,2,4-triazole; heterocyclization; multicomponent reaction; salicylaldehyde; ultrasonication; Introduction Multicomponent reactions (MCRs) are a powerful tool for the

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

• Elisandra Scapin,
• Paulo R. S. Salbego,
• Caroline R. Bender,
• Alexandre R. Meyer,
• Anderson B. Pagliari,
• Tainára Orlando,
• Geórgia C. Zimmer,
• Clarissa P. Frizzo,
• Helio G. Bonacorso,
• Nilo Zanatta and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 2396–2407, doi:10.3762/bjoc.13.237

• atom of the enone, both soft sites of the starting materials [29]. In recent research, we developed an efficient method to obtain 1,2,4-triazolo[1,5-a]pyrimidines from the cyclocondensation reaction of 1,1,1-trifluoro-4-metoxy-3-alken-2-one or β-enaminones with 5-amino-1,2,4-triazole. The methodology

2-Arylhydrazononitriles as building blocks in heterocyclic synthesis: A novel route to 2-substituted- 1,2,3-triazoles and 1,2,3-triazolo[4,5-b]pyridines

• Saleh M. Al-Mousawi and
• Moustafa Sh. Moustafa

Beilstein J. Org. Chem. 2007, 3, No. 12, doi:10.1186/1860-5397-3-12

• refluxing 2a with hydroxylamine hydrochloride in DMF/piperidine afforded 1,2,3-triazoles whose structure was established by X-ray crystal structure. [11] On the other hand reacting 2b with hydroxylamine hydrochloride in DMF/piperidine afforded 5-amino-1,2,4-triazole via a rare Tiemann-like rearrangement. In

• al, [14] and the possibility that the really formed product is the 5-amino-1,2,4-triazole 7. We decided to investigate further the chemical reactivity pattern of the cyclized product (Scheme 1) to support our conclusion. Compound 5 was reacted with malononitrile in refluxing DMF to yield the