Synthesis of isoniazid from 4-cyanopyridine

Sycheva, T. P.; Pavlova, T. N.; Shchukina, M. N.

doi:10.1007/bf00771896

Cited by 15 publications

(11 citation statements)

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“…was neutralized with AcOH and the formed precipitate was filtered off and crystallized from MeOH. 2, [6]. 2, 364.1227).…”

Section: Synthesis Of 124-triazole-3-thionesmentioning

confidence: 99%

“…2, [6]. 2, 364.1227). -4-(4,5-dihydro-4-butyl-5-thioxo-1H-1,2,4-triazol-3-yl (5) 1,2, ,2, 1,2, 2, -4-(4,5-dihydro-4-phenyl-5-thioxo-1H-1,2,4-triazol-3-yl -4-(4-butyl-4,5-dihydro-5-thioxo-1H-1,2,4-triazol-3-yl …”

Section: Synthesis Of 124-triazole-3-thionesmentioning

confidence: 99%

“…was neutralized with AcOH, the formed precipitate was filtered off, and crystallized from MeOH. 2, 2,4,4-tetramethylcyclobutane-1,3-dithione (10, 0.6 mmol) in CH 2 Cl 2 (1 ml) was added dropwise. The addition was complete after ca.…”

Section: -Benzylmentioning

confidence: 99%

“…-Acid hydrazides (carbohydrazides) and the corresponding hydrazones are well known as a class of compounds with diverse biological activities [1]. Particularly important are derivatives bearing a heterocycle, and one of the bestknown examples is isoniazid (isonicotinohydrazide) [2]. Imidazole derived hydrazides were also reported to display biological activity [3], and the majority of reports remain to patents (e.g., ref.…”

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confidence: 99%

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Synthesis of Bis‐Heterocyclic 1H‐Imidazole 3‐Oxides from 3‐Oxido‐1H‐imidazole‐4‐carbohydrazides

Pieczonka

Mlostoń

Heimgartner

2012

Helvetica Chimica Acta

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The reaction of 1H-imidazole-4-carbohydrazides 1, which are conveniently accessible by treatment of the corresponding esters with NH2NH2·H2O, with isothiocyanates in refluxing EtOH led to thiosemicarbazides (= hydrazinecarbothioamides) 4 in high yields (Scheme 2). Whereas 4 in boiling aqueous NaOH yielded 2,4-dihydro-3H-1,2,4-triazole-3-thiones 5, the reaction in concentrated H2SO4 at room temperature gave 1,3,4-thiadiazol-2-amines 6. Similarly, the reaction of 1 with butyl isocyanate led to semicarbazides 7, which, under basic conditions, undergo cyclization to give 2,4-dihydro-3H-1,2,4-triazol-3-ones 8 (Scheme 3). Treatment of 1 with Ac2O yielded the diacylhydrazine derivatives 9 exclusively, and the alternative isomerization of 1 to imidazol-2-ones was not observed (Scheme 4). It is important to note that, in all these transformations, the imidazole N-oxide residue is retained. Furthermore, it was shown that imidazole N-oxides bearing a 1,2,4-triazole-3-thione or 1,3,4-thiadiazol-2-amine moiety undergo the S-transfer reaction to give bis-heterocyclic 1H-imidazole-2-thiones 11 by treatment with 2,2,4,4-tetramethylcyclobutane-1,3-dithione (Scheme 5).

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“…was neutralized with AcOH and the formed precipitate was filtered off and crystallized from MeOH. 2, [6]. 2, 364.1227).…”

Section: Synthesis Of 124-triazole-3-thionesmentioning

confidence: 99%

Section: Synthesis Of 124-triazole-3-thionesmentioning

confidence: 99%

Section: -Benzylmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of Bis‐Heterocyclic 1H‐Imidazole 3‐Oxides from 3‐Oxido‐1H‐imidazole‐4‐carbohydrazides

Pieczonka

Mlostoń

Heimgartner

2012

Helvetica Chimica Acta

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“…• C under reflux conditions for 7 h. 17 The starting material, 4-cyanopyridine, is made from 4-picoline, which is expensive. Isoniazid can also be synthesized by refluxing ethyl isonicotinate with hydrazine hydrate.…”

Section: Introductionmentioning

confidence: 99%

Synergism of microwave irradiation and enzyme catalysis in synthesis of isoniazid

Yadav

Sajgure

2007

J of Chemical Tech & Biotech

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Isoniazid is a useful antitubercular drug widely employed in combination therapy with rifampicin. The synthesis of isoniazid from ethyl isonicotinate and hydrazine hydrate was studied in non-aqueous media via lipase-catalyzed hydrazinolysis under both conventional heating and microwave irradiation by using different supported lipases. Among three different commercial lipases used, namely Novozym 435 (Candida antarctica lipase), Lipozyme RM IM (Rhizomucor miehei lipase) and Lipozyme TL IM (Thermomyces lanuginosus lipase), Novozym 435 was found to be the most effective, with conversion of 54% for equimolar concentrations at 50• C in 4 h. The rate of reaction as well as final conversion increased synergistically under microwave irradiation in comparison with conventional heating, which showed 36.4% conversion, even after 24 h, for the control experiment. Effects of various process parameters such as speed of agitation, catalyst loading, substrate concentration, product concentration and temperature were studied. A kinetic model is also described.

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Recent Progress on Pyrazole Scaffold‐Based Antimycobacterial Agents

Keri

Chand

Ramakrishnappa

et al. 2015

Archiv der Pharmazie

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New and reemerging infectious diseases will continue to pose serious global health threats well into the 21st century and according to the World Health Organization report, these are still the leading cause of death among humans worldwide. Among infectious diseases, tuberculosis claims approximately 2 million deaths per year worldwide. Also, agents that reduce the duration and complexity of the current therapy would have a major impact on the overall cure rate. Due to the development of resistance to conventional antibiotics there is a need for new therapeutic strategies to combat Mycobacterium tuberculosis. Subsequently, there is an urgent need for the development of new drug candidates with newer targets and alternative mechanism of action. In this perspective, pyrazole, one of the most important classes of heterocycles, has been the topic of research for thousands of researchers all over the world because of its wide spectrum of biological activities. To pave the way for future research, there is a need to collect the latest information in this promising area. In the present review, we have collated published reports on the pyrazole core to provide an insight so that its full therapeutic potential can be utilized for the treatment of tuberculosis. In this article, the possible structure-activity relationship of pyrazole analogs for designing better antituberculosis (anti-TB) agents has been discussed and is also helpful for new thoughts in the quest for rational designs of more active and less toxic pyrazole-based anti-TB drugs.

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Synthesis of isoniazid from 4-cyanopyridine

Cited by 15 publications

References 0 publications

Synthesis of Bis‐Heterocyclic 1H‐Imidazole 3‐Oxides from 3‐Oxido‐1H‐imidazole‐4‐carbohydrazides

Synthesis of Bis‐Heterocyclic 1H‐Imidazole 3‐Oxides from 3‐Oxido‐1H‐imidazole‐4‐carbohydrazides

Synergism of microwave irradiation and enzyme catalysis in synthesis of isoniazid

Recent Progress on Pyrazole Scaffold‐Based Antimycobacterial Agents

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