Studies on the Reaction of Cycloalkanones with Malonodinitrile

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3‐(3,5‐Dimethyl‐1 H ‐pyrazol‐1‐yl)‐3‐oxopropanenitrile 1 was used as a cyanoacetylating agent for synthesis of the acetanilide derivative 3. Compound 3 was utilized as a key intermediate for the synthesis of some new mono‐chromene and di‐chromene derivatives 9 and 13, the dihydrazo derivatives 15, and the dithiazole derivatives 18 via the condensation with o‐hydroxybenzaldehyde derivatives, the coupling with aryl diazonium salts, or the reaction with phenyl isothiocyanate in presence of KOH followed by phenacyl bromide derivatives respectively.

Section: Introductionmentioning

confidence: 99%

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

Metwally

Abdelrazek

Eldaly

et al. 2015

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“…In the past two decades, we have been involved in a program aiming to synthesize new heterocyclic compounds of biological interest that may find applications as biodegradable agrochemicals from laboratory available cheap starting materials . In the context of this program, we have previously reported the synthesis of some 4‐hetaryl‐substituted chromene derivatives 3 as well as some 4‐hetaryl‐substituted pyrano[2,3‐ c ]pyrazole derivatives 5 (Scheme ) from the reaction of cyclic‐β‐diketones 1 or active methylene pyrazolones 4 with 2/3‐furfurylidene‐melononitrile or 2/3‐thienylidene‐malononitrile derivatives 2 , respectively, aiming to be evaluated as molluscicides .…”

Section: Introductionmentioning

confidence: 99%

An Eco‐friendly Synthesis of Some Novel 4‐methyl‐4‐hetaryl Chromene and Pyrano[2,3‐c]pyrazole Derivatives

Abdelrazek

Metz

Jäger

et al. 2017

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in Wiley Online Library (wileyonlinelibrary.com).Some novel chromene and pyrano [2,3-c]pyrazole derivatives could be achieved successfully by reacting cyclic β-diketones with 2-acetylfuran/2-acetylthiophene and malononitrile in a one-pot synthesis. Active methylene pyrazolones reacted with 2-(1-furan-2-yl-ethylidene)-malononitrile and 2-(1-thiophen-2-ylethylidene)-malononitrile derivatives to afford the desired pyrano[2,3-c]pyrazole derivatives. Structures of all new compounds were established based on analytical and spectral data as well as X-ray crystallography. A plausible mechanism for the reaction is suggested. The solvents and catalyst used are environmentally benign, and no hazardous solvents or heavy metals were involved. J. Heterocyclic Chem., 54, 2313 (2017. RESULTS AND DISCUSSIONSynthesis of the chromene derivatives 8a-d. Cyclohexa-1,3-dione 1a and dimedone 1b were allowed to react with 2-acetylfuran 6a/2-acetylthiophene 6b and malononitrile

“…Moreover, pyrazolo[1,5‐ a ]pyrimidines have an important synthetic value in the preparation of drugs with anticancer activities . In continuation of our interest in synthesis of some new bioactive heterocyclic compounds , we report herein the preparation of polyheterocycles from pyrazolo[1,5‐ a ]pyrimidine derivative. 2‐(Cyanomethyl)‐5,7‐dimethylpyrazolo[1,5‐ a ]pyrimidine‐3‐carbonitrile seemed to be a good candidate to fulfill this objective via its thioanilide derivative that has been unreported hitherto.…”

Section: Introductionmentioning

confidence: 99%

Pyrazolo[1,5‐a]Pyrimidine Derivative as Precursor for Some Novel Pyrazolo[1,5‐a]Pyrimidines and Tetraheterocyclic Compounds

Metwally

Abdallah

Al‐Mabrook

2016

The 2‐(cyanomethyl)‐5,7‐dimethylpyrazolo[1,5‐a]pyrimidine‐3‐carbonitrile 3 reacted with phenyl isothiocyanate to afford the respective thioanilide derivative 4 that is a novel compound that has been unreported hitherto. The latter was used as a precursor to synthesize several novel polyheterocyclic compounds 9, 12, 15, and 19. Treatment of the enamine derivative of compound 3 with each of hydrazine hydrate and hydroxylamine hydrochloride yielded the tetraheterocyclic compounds 22 and 23, respectively. The structures of all the newly synthesized compounds were confirmed on basis of their elemental, spectral data, and plausible mechanism has been postulated to account for their formation. X‐ray crystallography was carried out as a further evidence for the structure of the isolated product 19.