Activated nitriles in heterocyclic synthesis. IV. Reactions with 1‐ethoxycarbonyl‐4‐cyanoacetylthiosemicarbazide. Synthesis of Functionalized Pyridinone and 1,3,4‐Thiadiazole Derivatives

Ramiz, M. M. M.; El-Gandour, A. H.; Elagamey, A. A.

doi:10.1002/prac.19883300420

Cited by 6 publications

(2 citation statements)

References 3 publications

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“…Compounds 5a,b were purified by recrystallization from appropriate solvents. (60), 236 (51), 142 (23), 116 (16), 73 (25), 58 (22), 43 (24), 42 (22) (13), 187 (27), 172 (11), 156 (22), 142 (55), 134 (100), 130 (13), 115 (60), 102 (46), 89 (53), 77 (28), 63 (14), 51 (17), 42 (26), 29 (5) (7), 156 (20), 142 (15), 128 (14), 115 (75), 103 (6); 89 (13), 77 (10), 68 (10), 44 (38), 39 (10) (53), 251 (23), 157 (24), 142 (55), 115 (65), 89 (10), 77 (14), 36 (40)…”

Section: Resultsmentioning

confidence: 99%

Synthesis and reactions of pyrazolo[5,1-c][1,2,4]triazine-3-carbothioamides

Леденева

Didenko

Dotsenko

et al. 2013

Proceedings of the 17th International Electronic Conference on Synthetic Organic Chemistry

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Cyanothioacetamide reacts with pyrazole-3(5)-diazonium chlorides under mild conditions to afford pyrazolo[5,1-c][1,2,4]triazine-3-carbothioamides. The latter can be oxidized with H 2 O 2 to give either pyrazolo[5,1-c][1,2,4]triazine-3-carboxamides or 1,2,4-thiadiazole derivatives, depending on the reaction conditions. The Hantzsch-type reaction of thioamides 5 with α-bromo ketones leads to 3-(thiazol-2-yl)pyrazolo [5,1-c][1,2,4]triazines.

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Section: Resultsmentioning

confidence: 99%

Synthesis and reactions of pyrazolo[5,1-c][1,2,4]triazine-3-carbothioamides

Леденева

Didenko

Dotsenko

et al. 2013

Proceedings of the 17th International Electronic Conference on Synthetic Organic Chemistry

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“…These transformations also involved the formation of hydrazones 79, which either after specific treatment stage (or sometimes spontaneously) transformed into 4-amino derivatives of pyrazolo [5,1- Hetarylacetonitriles have been used for the construction of pyrazolotriazine 3-azolyl and 3-azinyl derivatives 81 from pyrazole diazonium salts [156][157][158][159][160][161][162]. There are examples of pyrazole diazonium salts 1 reacting with amides or hydrazides of cyanoacetic acid [92,128,[163][164][165] as well as its thioamide [166]. Similarly to the previous cases, as-triazine ring closure required the presence of nitrile group.…”

Section: Intermolecular Azo Couplingmentioning

confidence: 99%

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Ledenyova

Didenko

Shikhaliev

2014

Chem Heterocycl Comp

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The methods of synthesis, structure, reactivity, and synthetic utility of pyrazole-3(5)-diazonium salts are reviewed here for the first time, with emphasis on heterocyclization reactions of these compounds.More than one hundred years have passed since α-diazo derivatives of pyrazole were discovered. A substantial amount of knowledge has been accumulated over this time regarding the stability, structure, and transformations of these compounds. However, the chemistry of pyrazole-3(5)-diazonium salts developed rapidly only in the second half of the 20th century, with many studies performed in various countries, in particular Germany, Egypt, Russia, and Japan. Unfortunately, no systematic review has been compiled for the wide range of data about pyrazole-3(5)-diazonium salts. Some aspects regarding the properties of these compounds have been discussed in reviews and monographs on other topics [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17].

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