Behavior of 4-hydroxy-4-methyl-2-pentynonitrile in water in the presence of lithium hydroxide

Andriyankova, L. V.; Abramova, N. D.; Малькина, А. Г.; Skvortsov, Yu. M.

doi:10.1007/bf00957181

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“…In aqueous dioxane, the reaction of cyanoacetylene 1a with KCN afforded 3(2H)-furanone 11 (Scheme 11). 16 The hydroxide ion is added to acetylene 1 to generate intermediates A and A'. The latter are cyclized to hydroxyiminodihydrofuran B and iminodihydrofuran B', which are stabilized to produce 3(2H)-furanone 11.…”

Section: Methodsmentioning

confidence: 99%

“…The latter are cyclized to hydroxyiminodihydrofuran B and iminodihydrofuran B', which are stabilized to produce 3(2H)-furanone 11. 16 The reaction of cyanoacetylenic alcohols 1 with thiosemicarbazide, under physiological conditions proceeded in chemo-, regio-and stereoselective fashion to produced trifunctionalized (amino, hydroxyl and thioamide functions) pyrazoles 22a-d in up to 91% yield (Scheme 17). 19 Scheme 17 The synthesis of pyrazoles 22 from cyanoacetylenic alcohols 1 and thiosemicarbazide 19 This cyclization is rather unexpected.…”

Section: Methodsmentioning

confidence: 99%

“…Scheme 57 Synthesis of 4,15-dioxa-7,12-diazapentacyclo[9.5.2.0 2,10 .03,7 .012,16 ]octadeca-8,17-dienes 81 from cyanoacetylenic alcohols 1 and ethyl isonicotinate…”

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confidence: 99%

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Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides

Трофимов¹,

Малькина²

2021

Synthesis

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Cyanoacetylenic alcohols, R1R2C(OH)C≡C-CN, the closest derivatives of cyanoacetylene, an interstellar abundant molecule, are now becoming acknowledgeable in modern organic synthesis which tends to mimic nature. Highly reactive C≡C and C≡N bonds in close vicinity of the hydroxyl group makes these molecules a chemical trinity of mutually influencing functions ensuring an endless number of chemical transformations. All reactions of cyanoacetylenic alcohols parallel modern organic synthesis, being biomimetic. They do not need transition metals (and in most cases, the metals at all except for physiologically indispensible Na+, K+), proceed at ambient temperature and often in aqueous media. Fundamentally, these reactions are 100% atom-economic because they are almost exclusively addition processes. Usually, in the cyanoacetylenic alcohols, cyano, acetylene and hydroxyl functions behave as inseparable entity providing the multiple functionalizations of the forming molecules. This allows hydroxyl, carbonyl, carboxylic, imino, amino, amido, cyanoamido, cyano, various P-containing, ether and ester functions, along with the double bonds and different fundamental heterocycles (furans, furanones, pyrazoles, oxazoles, pyridines, pyrimidines, purins, etc.) and diverse polycyclic systems to be integrated in a one molecular architecture. This review focuses on analysis and generalization of the knowledge accumulated in the chemistry of these cyanoacetylenic alcohols, mostly over the past 15 years.

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Section: Methodsmentioning

confidence: 99%