Michael Reactions of Arylidenesulfonylacetonitriles. A New Route to Polyfunctional Benzo[a]quinolizines

Abdallah, Tayseer A.; Abdelhadi, Hyam A.; Hassaneen, Huwida M.; Hassaneen, Hamdi M.

doi:10.3390/70700540

Cited by 10 publications

(7 citation statements)

References 14 publications

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“…[24][25][26][27][28][29] In conjunction with this work we report here the synthesis of the starting 2-chloro-3-formyl-9,10-dimethoxy-4-oxo-6,7dihydro-4H-pyrido[2,1-a]isoquinoline-1-carbonitrile (3) (Scheme 1). Treatment of 1-cyanomethylisoquinoline 1 with diethyl malonate in nitrobenzene and refluxed for 30 min gave 2-hydroxy-9,10dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-a]isoquinoline-1-carbonitrile (2) in 92% yield.…”

Section: Resultsmentioning

confidence: 99%

“…[5][6][7][8][9][10][11][12][13][14][15][16][17] Recently, we have been involved in the synthesis and chemistry of several fused isoqinoline derivatives. [18][19][20][21][22][23][24][25][26][27][28][29] In the present paper, we introduce a new and general route to pyrido[2,1-a]isoquinoline containing many reactive sites. The aim of this study, on one hand is to prepare a novel tetracyclic compounds starting from readily obtainable materials in good yields and on the other hand, to prepare compounds that might have pharmacological activity.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Reactivity of 2-Chloro-3-formylpyrido[2,1-a]isoquinoline Derivative. A Novel Routes to Pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline and Isoquinolino[2,1-g][1,6]naphthyridines

Hassaneen¹,

Wardkhan²,

Mohammed³

2012

HETEROCYCLES

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Treatment of 2-hydroxy-9,10-dimethoxy-4-oxo-6,7-dihydro-4Hpyrido[2,1-a]isoquinoline-1-carbonitrile 2 with POCl 3 /DMF gave 2-chloro-3formylpyrido[2,1-a]isoquinoline derivative 3. Compound 3 reacted with hydrazines 5a-d to give the condensation products 6a-d. Cyclization of 6a gave pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline derivative 7. Treatment of 3 with ethoxycarbonylmethylenetriphenylphosphorane 10 afforded (E)-ethyl 3-(2chloro-1-cyano-9,10-dimethoxy-4-oxo-6,7-dihydro-4H-pyrido[2,1-a]isoquinolin-3-yl)acrylate 11. Azidation of 11 yielded the corresponding azido compound 12.Reduction of 12 gave the corresponding amino compound 13 which upon cyclization gave the novel tetracyclic product 14. Compound 12 reacted with triphenylphosphine to give phosphorane compound 15, which reacted with phenyl isothiocyanate to give a novel isoquinolino[2,1-g][1,6]naphthyridine derivative 18.Refluxing of 11 with amines 19a-c and thiophenols 22a-d in ethanol produced the corresponding substitution products 20a-c and 23a-d, respectively. Cyclization of 20a afforded isoquinolino[2,1-g][1,6]naphthyridine derivative 21.of the information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Tel: +44 (0)1223 762911; www: http://www.ccdc.cam.ac.uk).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactivity of 2-Chloro-3-formylpyrido[2,1-a]isoquinoline Derivative. A Novel Routes to Pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline and Isoquinolino[2,1-g][1,6]naphthyridines

Hassaneen¹,

Wardkhan²,

Mohammed³

2012

HETEROCYCLES

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“…High yielding syntheses of polyfunctional benzo[a]quinolizines are well-documented [264]. Abdallah et al [265] reported a new and general one-step route affording polyfunctional substituted benzo[a] quinolizines in good yield from readily available inexpensive starting materials using isoquinoline derivatives. Thus, treatment of 1-methyl isoquinoline 334 with arylidenesulfonylacetonitriles 333 in boiling acetonitrile in the presence of an equimolar amount of piperidine leads, in each case, to the formation of only one product 337 and 338, as indicated by TLC and 1H-NMR analysis.…”

Section: Scheme 111mentioning

confidence: 99%

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Elgazwy¹

2013

Organic Chem Current Res

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including purines [7,8], pyrimidines [9], pyrazines [10] (some which are widely employed in the fluorescent dye industry [11]), imidazoles [12], biphenylenes [13], porphyrazines (which have great potential in optical sensor technology) [14] and diimines that are used as catalysts [15]. This review highlights the alkenyl nitrile chemistry with the focus on the utility of heterocyclic compounds. The synthesis and chemistry of the highly strained aryl nitrile is also briefly reviewed [16]. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into an structure, probably the use of a alkenyl nitrile analogue is the most direct one. The present review deals with the generation and synthetic uses of alkenyl nitriles and aryl nitriles formed in heterocyclic synthesis, and can be considered as an update of our revision published in 2007 on this topical [17]. Therefore, only references published from the second quarter of 2003 until the third quarter of 2010 are included, and the same restrictions to the literature coverage applied. Thus, only heterocycles compounds which are found applicability are considered. As previously, the present review is organized by the type of ring members and subdivided by the type of heterocycles fused compounds, including methods for their preparation and their synthetic uses. New developments in the utilities of some alkenyl nitriles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of alkenyl nitriles of active imines are discussed. The major methods and modifications are analyzed [18-21]. In this review, which covers the literature up to date, we describe the new and improved methods for the construction of the skeletons, with a particular emphasis on the four, five and six membered ring of heterocyclic compounds. Some of these procedures have clear technical advantages over older methods in terms of yield and versatility, but do not employ new chemistry in the construction of the ring systems. The

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“…Also, benzo[a]isoquinolines have been associated with a variety of interesting pharmacological properties, among which chemotherapeutic , neuroleptic , anticonvulsant , and anti‐inflammatory . Our research group for 15 years has been focusing on the synthesis of isoquinoline‐containing compounds, and a variety of chemically diverse structures with biological and antitumor activity were obtained . In addition, we have also been interested in the search of new compounds with antitumor properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactions of Pyrido[2,1‐a]isoquinolin‐4‐yl Formimidate Derivatives and Antimicrobial Activities of Isolated Products

Hassaneen

Wardakhan

Mohammed

2017

Journal of Heterocyclic Chem

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Treatment of arylidene malononitriles 2A–C with 1‐cyanomethylisoquinoline 1 afforded 4‐amino‐2‐arylpyrido[2,1‐a]isoquinoline‐1,3‐dicarbonitrile derivatives 5A–C, which converted to formimidates 6A–C via reaction with triethylorthoformate. Treatment of the latter compounds with hydrazine hydrate gave the corresponding amino–imino compounds 7A–C, which underwent Dimroth rearrangement to afford 13‐aryl‐1‐hydrazinylpyrimido[5′,4′:5,6]pyrido[2,1‐a]isoquinoline‐12‐carbonitrile 8A–C. The latter reacted with aldehyde to give 9a–i. Oxidative cyclization of the latter compounds 9a–i gave [1,2,4]triazolo[4″,3″:1′,6′]‐pyrimido[5′,4′:5,6]pyrido[2,1‐a]isoquinolines 10a,d,g. Such compounds isomerized to the thermodynamically more stable isomers [1,2,4]triazolo[1″,5″:1′,6′]pyrimido[5′,4′:5,6]‐pyrido[2,1‐a]isoquinolines 11a,d,g. Antimicrobial activities for some compounds were studied.

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Michael Reactions of Arylidenesulfonylacetonitriles. A New Route to Polyfunctional Benzo[a]quinolizines

Cited by 10 publications

References 14 publications

Synthesis and Reactivity of 2-Chloro-3-formylpyrido[2,1-a]isoquinoline Derivative. A Novel Routes to Pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline and Isoquinolino[2,1-g][1,6]naphthyridines

Synthesis and Reactivity of 2-Chloro-3-formylpyrido[2,1-a]isoquinoline Derivative. A Novel Routes to Pyrazolo[3',4':4,5]pyrido[2,1-a]isoquinoline and Isoquinolino[2,1-g][1,6]naphthyridines

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Synthesis and Reactions of Pyrido[2,1‐a]isoquinolin‐4‐yl Formimidate Derivatives and Antimicrobial Activities of Isolated Products

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