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 | 2019-11-21T06:21:29Z | |
dc.date.available | 2019-11-21T06:21:29Z | |
dc.date.issued | 2015 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/55857 | |
dc.description.abstract | 2-Amino-N′-phenylbenzamidine (1a) reacts with tetracyanoethene (TCNE) to give 2-[2-(2-aminophenyl)-5-imino-1-phenyl-1H-imidazol-4(5H)-ylidene]malononitrile (11a), 4-(phenylamino)quinazoline-2-carbonitrile (5a) and 4-imino-3-phenyl-3,4-dihydroquinazoline-2-carbonitrile (9a). By optimizing the reaction conditions each of the compounds can be isolated as the main product and seven examples of these reactions are described. The [1H-imidazol-4(5H)-ylidene]malononitrile 11a was also independently synthesized in three steps from 2-amino-N′-(2-nitrophenyl)benzamidine (25) and TCNE in an overall yield of 56%. Dimroth rearrangement of either 2-aminophenyl- or 2-nitrophenyl-substituted [1H-imidazol-4(5H)-ylidene]malononitriles 11a or 27 with DBU in hot DCM gave the 2-[2-(2-aminophenyl)- and 2-[2-(2-nitrophenyl)-5-(phenylimino)-3H-imidazol-4(5H)-ylidene]malononitriles 28 (71%) and 34 (59%), respectively. Treatment of the [3H-imidazol-4(5H)-ylidene]malononitrile 28 with ethyl orthoformate in DMA at 165°C gave (Z)-2-[3-(phenylimino)imidazo[1,2-c]quinazolin-2(3H)-ylidene]malononitrile (36) (70%), thermolysis of which gave quinolino[3′,2′:4,5]imidazo[1,2-c]quinazoline-13-carbonitrile (30) (97%). © 2015 Elsevier Ltd. | en |
dc.source | Tetrahedron | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-84943770070&doi=10.1016%2fj.tet.2015.09.049&partnerID=40&md5=63aec395bcd81662e1121825ed5c8164 | |
dc.subject | priority journal | en |
dc.subject | unclassified drug | en |
dc.subject | Article | en |
dc.subject | Quinazolines | en |
dc.subject | crystal structure | en |
dc.subject | cyclization | en |
dc.subject | Heterocycles | en |
dc.subject | imidazole derivative | en |
dc.subject | hydrogen | en |
dc.subject | Cyclization reactions | en |
dc.subject | malononitrile | en |
dc.subject | cyanide | en |
dc.subject | Tetracyanoethylene | en |
dc.subject | quinazoline derivative | en |
dc.subject | 2 [2 (2 aminophenyl) 5 imino 1 phenyl 1h imidazol 4(5h) ylidene]malononitrile | en |
dc.subject | 2 [2 (2 nitrophenyl) 5 (phenylimino) 3h imidazol 4(5h) ylidene]malononitrile | en |
dc.subject | 2 [3 (phenylimino)imidazo[1,2 c]quinazolin 2(3h) ylidene]malononitrile | en |
dc.subject | 2 amino n phenylbenzamidine | en |
dc.subject | 2 amino n' (2 nitrophenyl)benzamidine | en |
dc.subject | 4 (phenylamino)quinazoline 2 carbonitrile | en |
dc.subject | 4 imino 3 phenyl 3,4 dihydroquinazolin 2 carbonitrile | en |
dc.subject | Amidines | en |
dc.subject | ethyl orthoformate | en |
dc.subject | ethylene | en |
dc.subject | Imidazoles | en |
dc.subject | quinolino[2',3':4,5]imidazo[1,2 c]quinazoline 8 carbonitrile | en |
dc.subject | quinolino[3',2':4,5]imidazo[1,2 c]quinazoline13 carbonitrile | en |
dc.subject | tetracyanoethene | en |
dc.title | The reaction of 2-amino-N′-arylbenzamidines with tetracyanoethene reinvestigated: routes to imidazoles, quinazolines and quinolino[2′,3′:4,5]imidazo[1,2-c]quinazoline-8-carbonitrile | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1016/j.tet.2015.09.049 | |
dc.description.volume | 71 | |
dc.description.issue | 46 | |
dc.description.startingpage | 8766 | |
dc.description.endingpage | 8780 | |
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.source.abbreviation | Tetrahedron | 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 | |