A Facile Access for Synthesis of Novel Isoquinoline-Based Heterocycles

Hassaneen, Hamdi M.; Abdallah, Tayseer A.; Awad, Enas M.

doi:10.3987/com-09-11648

Cited by 10 publications

(23 citation statements)

References 22 publications

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“…Therefore, the synthesis of this ring system is an attractive goal. We have previously reported the syntheses of triazoloisoquinoline and fused isoquinoline compounds via reaction of 3,4-dihydro-6,7-dimethoxyisoquinoline derivatives with hydrazonoyl halides in chloroform in the presence of triethylamine or in pyridine as catalyst and solvent [8][9][10][11][12]. The aim of the present study is to introduce a new synthetic method by replacing triethylamine in chloroform by the ecologically more acceptable catalyst chitosan [13,14] and under microwave irradiation to enhance reaction rates [15][16][17][18][19] for the synthesis of [1,2,4]triazolo [3,4-a]isoquinolines which were found to be useful precursors for the synthesis of new enaminones 7.…”

Section: Introductionmentioning

confidence: 99%

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

Hassaneen¹,

Mohammed²

2011

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The reaction of 1-methylisoquinoline 1 with hydrazonoyl halides 2 in ethanol in the presence of chitosan under microwave irradiation affords triazoloisoquinoline 4. Product 4 reacts with dimethylformamide-dimethylacetal to give enaminones 7 which react with hydrazonoyl halides to give pyrazolyl triazoloisoquinoline 13. Also, 1-methylisoquinoline 1 reacts with arylisothiocyanate to give thioanilide 15 which reacts with hydrazonoyl halides to give the corresponding thiadiazolyl isoquinoline derivatives 20, 24.

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Section: Introductionmentioning

confidence: 99%

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

Hassaneen¹,

Mohammed²

2011

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“…It was claimed that 3-aroyl-3-hydroxyimino-2-(6,7-dimethoxy-1,2,3,4-tetra-hydroisoquinolin-1-ylidene)propanenitrile (18) can be obtained in good yield from the reaction of hydroxamoyl chlorides 16a-f with 1 (Scheme 5) [27]. In our hands, stirring of 1 with 16a in acetonitrile at room temperature afforded a product which gave analytical data consistent with its formulation as 2-benzoyl-8,9-dimethoxy-5,6-dihydropyrazolo[5,1-a]isoquinoline-1-carbonitrile 19a.…”

Section: Resultsmentioning

confidence: 99%

A Novel Route to Isoquinoline[2,1-g][1,6]naphthyridine, Pyrazolo[5,1-a] isoquinoline and Pyridazino[4´,5´:3,4]pyrazolo[5,1-a]isoquinoline Derivatives With Evaluation of Antitumor Activities

Hassaneen

Wardkhan

Mohammed

2013

Zeitschrift Für Naturforschung B

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(E)-2-Chloro-3-(2-cyanovinyl)-9,10-dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-a] isoquinoline-1-carbonitrile (5) was obtained by treatment of the 2-chloro-3-formylpyrido[2,1-a]isoquinoline derivative 3 with 2-(triphenylphosphoranylidene)acetonitrile (4). Treatment of 5 with sodium azide afforded the corresponding azido compound 6 which could be reduced by sodium dithionite to compound 7. A novel isoquinolino[2,1-g][1,6]naphthyridine derivative 11 was obtained by the reaction of phenyl isothiocyanate with the phosphorane compound 8, which was prepared by the reaction of compound 6 with triphenylphosphine. Treatment of 5 with amines 12a-c and thiophenols 14a-c in refluxing ethanol afforded the corresponding substitution products 13a-c and 15a-c, respectively. Also, the reaction of 1 with α-oxo hydroxamoyl chlorides 16 was reinvestigated, and the synthesized pyrazoloisoquinolines 19a-f and pyridazinopyrazoloisoquinolines 20a, e were screened for their in vitro antitumor activities.

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“…Furthermore, attempts to prepare the isomeric pyrazol [4,3-e] [1,2,4]triazolo [4,3-c] pyrimidines via dehydrative cyclization of the 4-acylhydrazinopyrazolo [3,4-d]pyrimidines were reported to give the corresponding pyrazolo [4,3-e] [1,2,4]triazolo [1,5-c]pyrimidines. [7] In the light of these findings and in continuation of our ongoing research work on the chemistry of hydrazonoyl halides, [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] it was thought interesting to synthesize new series of pyrazolo [3,4-d]pyrimidine and pyrazolo [4,3-e] [1,2,4]triazolo [3,4-c]pyrimidine derivatives. Evaluation of antimicrobial activity against some microorganisms was investigated.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4‐d]pyrimidine, pyrazolo[4,3‐e][1,2,4]triazolo[1,5‐c]pyrimidine, and pyrazolo[4,3‐e][1,2,4]triazolo[3,4‐c]pyrimidine derivatives

Hassaneen

Saleh

Abdallah

et al. 2019

Journal of Heterocyclic Chem

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Treatment of N-phenyl-substituted benzenecarbo-hydrazonoyl chlorides 1ad with malononitrile in sodium ethoxide solution gave 5-amino-4-cyanopyrazole derivatives 2-5. Compounds 2-5 were converted to formidate derivatives 6-9 upon treatment with TEOF in acetic anhydride. The reaction of the latter products 6-9 with hydrazine hydrate gave imino-amino derivatives 10-13, which was converted to hydrazino derivatives 14-17 by refluxing with hydrazine hydrate. Hydrazino as well as imino-amino derivatives undergo condensation, cyclization, and cycloaddition reactions to give pyrazolo[3,4-d]pyrimidine 18-21, pyrazolo[4,3-e][1,2,4]triazolo-[3,4-c]pyrimidine 22-27, and pyrazolo[3 0 ,4 0 :4,5]pyrimido[1,6-b][1,2,4]triazine 42-44 derivatives. Antimicrobial studies are performed using two Gram-positive bacteria and two Gram-negative bacteria. Data indicated that compounds 5, 28D, 29B, and 31D are exploring elevated antibacterial effects against all strains tested. Compound 28D is the most promising antibacterial agent against the delicate bacterial strain Bacillus subtilis and Pseudomonas aeruginosa with high effectiveness (low minimum inhibitory concentration [MIC] value) 40 and 60 μg/mL, respectively.

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A Facile Access for Synthesis of Novel Isoquinoline-Based Heterocycles

Cited by 10 publications

References 22 publications

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

A Novel Route to Isoquinoline[2,1-g][1,6]naphthyridine, Pyrazolo[5,1-a] isoquinoline and Pyridazino[4´,5´:3,4]pyrazolo[5,1-a]isoquinoline Derivatives With Evaluation of Antitumor Activities

Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4‐d]pyrimidine, pyrazolo[4,3‐e][1,2,4]triazolo[1,5‐c]pyrimidine, and pyrazolo[4,3‐e][1,2,4]triazolo[3,4‐c]pyrimidine derivatives

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