Heterocyclic analogs of pleiadiene

Пожарский, А. Ф.; Konstantinchenko, A. A.; Kashparov, I. S.

doi:10.1007/bf00635954

Cited by 3 publications

(2 citation statements)

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“…Irradiation (at λ = 313 nm, 30 min) of 28 (0.5 g) in methanol (100 mL) apportioned in eight pyrex vessels and chromatography gave the 3-(acetylamino)-1-methylindazole ( 33 ), (0.15 g; 30%), mp 142 °C (from water) (lit 12a. mp 142 °C), and then the 2-(acetylamino)-1-methylbenzimidazole ( 36 ) (0.25 g; 50%), mp 182 °C (from methanol) (lit . mp 182 °C).…”

Section: Methodsmentioning

confidence: 99%

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Photoinduced Molecular Rearrangements. The Photochemistry of Some 1,2,4-Oxadiazoles in the Presence of Nitrogen Nucleophiles. Formation of 1,2,4-Triazoles, Indazoles, and Benzimidazoles

1996

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The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles [external, such as added amines or hydrazines, or internal, such as an o-aminophenyl moiety at C(3) of the oxadiazole ring] has been investigated. In the irradiation of 5-amino-(or 5-N-substituted amino) 3-phenyl-1,2,4-oxadiazoles in the presence of aliphatic primary amines (or ammonia), photolytic species arising from heterolytic cleavage of the ring O−N bond capture the nucleophilic reagent to give open-chain intermediates, which develop into 1,2,4-triazolin-5-ones. Similarly, irradiations of 3,5-diphenyl-, 3-methoxy-5-phenyl-, and 5-methyl-3-phenyl-1,2,4-oxadiazoles gave 1,2,4-triazoles. In the same context, irradiations of representative substrates in the presence of hydrazines have been also investigated. In the irradiation of 3-(o-aminophenyl)-5-methyl-, 3-[o-(methylamino)phenyl]-5-methyl-, and 3-(o-aminophenyl)-5-phenyl-1,2,4-oxadiazoles, concomitant formation of indazoles and benzimidazoles, presumably arising from a common photolytic species, has been observed. Some mechanistic aspects have been considered, and possible applications in synthesis have been pointed out.

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Section: Methodsmentioning

confidence: 99%

“…12a mp 142 °C), and then the 2-(acetylamino)-1-methylbenzimidazole (36) (0.25 g; 50%), mp 182 °C (from methanol) (lit. 36 mp 182 °C). Analytical photochemistry as above gave 33 (30%) and 36 (70%).…”

Section: Mp 195 °C)mentioning

confidence: 99%

Photoinduced Molecular Rearrangements. The Photochemistry of Some 1,2,4-Oxadiazoles in the Presence of Nitrogen Nucleophiles. Formation of 1,2,4-Triazoles, Indazoles, and Benzimidazoles

1996

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Perimidines: a unique π-amphoteric heteroaromatic system

et al. 2020

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Data on the physicochemical characteristics, theoretical calculations, reactivity and synthetic methods for perimidines are summarized. Although perimidine and some of its simple 2-substituted derivatives were obtained by Sachs back in 1909, their chemistry and key physical properties remained unknown until the early 1970s. Subsequent studies revealed many fundamental features of the perimidine system, previously not encountered in the heterocyclic series. The first comprehensive review on perimidines was published forty years ago. The period that has passed since 1980 led to the emergence of new directions and trends. Several hundred new publications have appeared, the generalization of which has become the main purpose of this article. This primarily concerns the obtaining of highly nucleophilic and stable perimidine carbenes, new methods of electrophilic substitution and oxidation, establishment of a close relationship between perimidines and proton sponges, and modern theoretical calculations. Based on perimidines, many different polycondensed systems have been obtained. Applied research has developed especially rapidly in recent years. Many new compounds based on perimidines related to chemosensors, analytical reagents, dyes, metal catalysts, electronic devices, nanotechnology, and medical chemistry have been proposed. Some information under review is presented as Supplementary Materials. It contains six tables, which include data on the basicity constants of perimidines, details of some synthetic methods for perimidines and fused analogs and also a list of biological activities of perimidines. The bibliography includes 387 references.

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