ChemInform Abstract: Nitroazines. Part 8. Reaction of 6‐Nitroazolo(1,5‐a)pyrimidines (I) with Pyrroles (II).

Pilicheva, T. L.; Русинов, В. Л.; Tumashov, A. A.; Чупахин, О. Н.

doi:10.1002/chin.198917225

Cited by 1 publication

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“…Two isomers 194a and 194b were detected in the reaction mixtures using pyrrole and N‐methylpyrrole [285] . The similar reaction with indole was also described for analogous electron‐deficient heterocycles: 6‐nitrotetrazolo[1,5‐ a ]pyrimidine [91,279] and 2,3‐cyanoderivative of 6‐nitroimidazo[1,2‐ a ]pyrimidine [91] …”

Section: Alternative Ways Of Dihydroazolopyrymidines Formationsupporting

confidence: 65%

“…The electron‐excessive phenols work as C‐nucleophiles: the use of flavonoid quercetin [282] resulted in formation of 193 , the use of other phenols [279,283,284] and N,N‐dialkylaminobenzenes [34] provided 7‐aryl‐6‐nitro‐4,7‐dihydro‐[1,2,4]triazolo[1,5‐ a ]pyrimidines 193 . Electron‐excessive heterocycles: pyrroles, [279,285,286] indoles [13,279] and thiophene [279] also acted as nucleophiles in the same mode resulting in formation of adducts 194a and 195 , correspondingly. Water [287,288] and ethanol [287] reacted as O‐nucleophiles (products 196 ).…”

Section: Alternative Ways Of Dihydroazolopyrymidines Formationmentioning

confidence: 99%

“…In the earlier work [285] authors analyzed the reaction mixture of the reaction of compound 188 with pyrroles using 1 H NMR spectroscopy and showed that besides main products 194a it contained minor amounts of positional isomers 194b (Scheme 71).…”

Section: Alternative Ways Of Dihydroazolopyrymidines Formationmentioning

confidence: 99%

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Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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Dihydroazolopyrimidines are an important class of heterocycles that are isosteric to natural purines and are therefore of great interest primarily as drug‐like molecules. In contrast to the heteroaromatic analogs, synthetic approaches to these compounds were developed much later, and their chemical properties and biological activity have not been studied in detail until recently. In the review, different ways to build dihydroazolopyrimidine systems from different building blocks are described – via the initial formation of a partially hydrogenated pyrimidine ring or an azole ring, as well as a one‐pot assembly of azole and azine fragments. Special attention is given to modern approaches: multicomponent reactions, green chemistry, and the use of non‐classical activation methods. Information on the chemical properties of dihydroazolopyrimidines and the prospects for their use in the design of drugs of various profiles are also summarized in this review.

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Section: Alternative Ways Of Dihydroazolopyrymidines Formationsupporting

confidence: 65%