Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Preparation and computational analysis of non symmetrical zwitterionic biscyanines
dc.contributor.author | Ioannou, Theodosia A. | en |
dc.contributor.author | Koutentis, Panayiotis Andreas | en |
dc.contributor.author | Krassos, H. | en |
dc.contributor.author | Loizou, G. | en |
dc.contributor.author | Re, D. L. | en |
dc.creator | Ioannou, Theodosia A. | en |
dc.creator | Koutentis, Panayiotis Andreas | en |
dc.creator | Krassos, H. | en |
dc.creator | Loizou, G. | en |
dc.creator | Re, D. L. | en |
dc.date.accessioned | 2019-11-21T06:19:30Z | |
dc.date.available | 2019-11-21T06:19:30Z | |
dc.date.issued | 2012 | |
dc.identifier.issn | 1477-0520 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/55582 | |
dc.description.abstract | Regioselective nucleophilic addition of bisnucleophiles 1,2-benzenediamine, 2-amino-benzenethiol, and N-phenyl-1,2-benzenediamine to 1,3-diphenylbenzo[e] [1,2,4]triazin-7(1H)-one (1) at C6 followed by intramolecular cyclocondensation at the C7 carbonyl afforded highly coloured tetracenes 1,3-diphenyl-1,6-dihydro- [1,2,4]triazino[5,6-b]phenazin-4-ium 4-methylbenzenesulfonate (12), 1,3-diphenyl-1H-[1,2,4]triazino[6,5-b]phenothiazine (14) and 1,3,11-triphenyl-1,6-dihydro-[1,2,4]triazino[5,6-b]phenazin-11-ium 4-methylbenzenesulfonate (15), respectively. Neutralization of the latter with alkali gave the free base 1,3,11-triphenyl-1H-[1,2,4]triazino[5,6-b]phenazin-11- ium-6-ide (16). Furthermore, the benzotriazinone 1 reacts with dimethyl malonate to give 6-(methoxycarbonyl)-7-oxo-1,3-diphenyl-7H-benzofuro[5,6-e][1,2,4] triazin-1-ium-4-ide (17) in 74% yield, while with S 4N 4 [5,6-c]-thiadiazolo-7-oxo-1,3-diphenyl-1,2,4-benzotriazine (22) was formed in 15% yield. The free bases 16 and 17 display negative solvatochromism, which supports charge separated ground states similar to those of zwitterionic biscyanines, and DFT calculations at the UB3LYP/6-31G(d) level afford ΔE ST values of -13.6 and -18.7 kcal mol -1, respectively that strongly favour the singlet ground state. All ring systems described are new and fully characterized. © 2012 The Royal Society of Chemistry. | en |
dc.source | Organic and Biomolecular Chemistry | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-84856692562&doi=10.1039%2fc1ob06622f&partnerID=40&md5=790f8a7178ac09ab540d9c8aaccb04c1 | |
dc.subject | DFT calculation | en |
dc.subject | Density functional theory | en |
dc.subject | Ground state | en |
dc.subject | Addition reactions | en |
dc.subject | Singlet ground state | en |
dc.subject | Computational analysis | en |
dc.subject | Cyclization | en |
dc.subject | Cyclization reactions | en |
dc.subject | Cyclocondensation | en |
dc.subject | Dimethyl malonate | en |
dc.subject | Free base | en |
dc.subject | Free basis | en |
dc.subject | Human echovirus 1 | en |
dc.subject | Regioselective nucleophilic addition | en |
dc.subject | Ring systems | en |
dc.subject | Solvatochromisms | en |
dc.title | Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: Preparation and computational analysis of non symmetrical zwitterionic biscyanines | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1039/c1ob06622f | |
dc.description.volume | 10 | |
dc.description.issue | 7 | |
dc.description.startingpage | 1339 | |
dc.description.endingpage | 1348 | |
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 :13</p> | en |
dc.source.abbreviation | Org.Biomol.Chem. | en |
dc.contributor.orcid | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] | |
dc.gnosis.orcid | 0000-0002-4652-7567 |
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