dc.contributor.author | Mirallai, Styliana I. | en |
dc.contributor.author | Manoli, Maria | en |
dc.contributor.author | Koutentis, Panayiotis Andreas | en |
dc.creator | Mirallai, Styliana I. | en |
dc.creator | Manoli, Maria | en |
dc.creator | Koutentis, Panayiotis Andreas | en |
dc.date.accessioned | 2019-11-21T06:21:30Z | |
dc.date.available | 2019-11-21T06:21:30Z | |
dc.date.issued | 2013 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/55859 | |
dc.description.abstract | Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared in four steps from N′-arylbenzamidines 11 and tetracyanoethylene (TCNE) in ∼70-90% yields. The transformation involves the initial formation of N-aryl-N′-(1,2,2-tricyanovinyl)benzamidines 12 in 87-99% yields, which in MeCN undergo a 5-exodig cyclization to give the 2-[1-aryl-5-imino-2-phenyl-1H- imidazol-4(5H)-ylidene]malononitriles 13 in 84-92% yields, while in MeOH the (Z)-2-[2-phenyl-4-(arylimino)-1H-imidazol-5(4H)-ylidene]malononitriles 14 are formed in 85-94% yields. The imidazoles 14 can also be prepared directly from imidazoles 13 via a Dimroth rearrangement in either neat MeOH or in DCM with DBU. Subsequent thermolysis of imidazoles 14 in diphenyl ether affords 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 in near quantitative yields. Mechanistic rationale is provided for all transformations. © 2013 American Chemical Society. | en |
dc.source | Journal of Organic Chemistry | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-84883772188&doi=10.1021%2fjo4013699&partnerID=40&md5=516068701e7b1d587fa2e10603008d6e | |
dc.subject | article | en |
dc.subject | unclassified drug | en |
dc.subject | Nitriles | en |
dc.subject | synthesis | en |
dc.subject | chemical reaction | en |
dc.subject | heat treatment | en |
dc.subject | reaction analysis | en |
dc.subject | Chemistry | en |
dc.subject | Molecular Structure | en |
dc.subject | methanol | en |
dc.subject | quinoline derivative | en |
dc.subject | cyclization | en |
dc.subject | Organic compounds | en |
dc.subject | imidazole derivative | en |
dc.subject | thermolysis | en |
dc.subject | quantum yield | en |
dc.subject | cyanide | en |
dc.subject | benzene derivative | en |
dc.subject | polycyclic aromatic hydrocarbon derivative | en |
dc.subject | Quantitative yields | en |
dc.subject | Tetracyanoethylene | en |
dc.subject | benzamidine derivative | en |
dc.subject | Imidazoles | en |
dc.subject | 2 phenyl 3h imidazo[4,5 b]quinoline 9 carbonitrile | en |
dc.subject | Benzamidines | en |
dc.subject | biotransformation | en |
dc.subject | Dimroth rearrangement | en |
dc.subject | Diphenyl ether | en |
dc.subject | ether derivative | en |
dc.subject | ethylene derivative | en |
dc.subject | Ethylenes | en |
dc.subject | Malononitriles | en |
dc.subject | Quinolines | en |
dc.title | Reactions of tetracyanoethylene with N′-arylbenzamidines: A route to 2-phenyl-3 H -imidazo[4,5- b ]quinoline-9-carbonitriles | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1021/jo4013699 | |
dc.description.volume | 78 | |
dc.description.issue | 17 | |
dc.description.startingpage | 8655 | |
dc.description.endingpage | 8668 | |
dc.author.faculty | 002 Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences | |
dc.author.department | Τμήμα Χημείας / Department of Chemistry | |
dc.type.uhtype | Article | en |
dc.description.notes | <p>Cited By :4</p> | en |
dc.source.abbreviation | J.Org.Chem. | en |
dc.contributor.orcid | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] | |
dc.contributor.orcid | Mirallai, Styliana I. [0000-0002-8195-8741] | |
dc.gnosis.orcid | 0000-0002-4652-7567 | |
dc.gnosis.orcid | 0000-0002-8195-8741 | |