dc.contributor.author | Koutentis, Panayiotis Andreas | en |
dc.contributor.author | Michaelidou, Sophia S. | en |
dc.creator | Koutentis, Panayiotis Andreas | en |
dc.creator | Michaelidou, Sophia S. | en |
dc.date.accessioned | 2019-11-21T06:20:33Z | |
dc.date.available | 2019-11-21T06:20:33Z | |
dc.date.issued | 2010 | |
dc.identifier.uri | http://gnosis.library.ucy.ac.cy/handle/7/55730 | |
dc.description.abstract | 2-Cyano cyanothioformanilide 3a reacts with triphenylphosphine in the presence of water to give 2-(cyanomethyleneamino)benzonitrile 4a, 2-(cyanomethylamino)benzonitrile 5, 3-aminoindole-2-carbonitrile 2a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 6a. In the presence of p-toluenesulfonic acid in MeOH the reaction between 2-cyano cyanothioformanilide 3a and triphenylphosphine (2 equiv) gives 3-aminoindole-2-carbonitrile 2a in 90% yield. Under the same conditions 2-(cyanomethyleneamino)benzonitrile 4a gives anthranilonitrile 8a, 3-aminoindole-2-carbonitrile 2a and N-(2-cyanophenyl)formamide 9. In addition, substituted 2-cyano cyanothioformanilides 3b-f react with triphenylphosphine and p-toluenesulfonic acid in MeOH to give 3-aminoindole-2-carbonitriles 2b-f in 63-75% yields. Under analogous conditions 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 2g gives only 4,5-dimethoxyanthranilonitrile 8g and 4,6,7-trimethoxyquinazoline-2- carbonitrile 14g, but in refluxing dry PhMe in the absence of p-toluenesulfonic acid 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 3g, (2-cyano-5,6- dimethoxyindol-3-yl)iminotriphenylphosphorane 6g and 2-(cyanomethyleneamino)-4, 5-dimethoxybenzonitrile 4g are obtained. The structure of 2- (cyanomethyleneamino)-4,5-dimethoxybenzonitrile 4g is supported unambiguously via independent synthesis and comparison to the isomeric 6,7- dimethoxyquinazoline-2-carbonitrile 15. All new compounds are fully characterised and a tentative mechanism for the transformation of 2-cyano cyanothioformanilides to indoles is proposed. © 2010 Elsevier Ltd. All rights reserved. | en |
dc.source | Tetrahedron | en |
dc.source.uri | https://www.scopus.com/inward/record.uri?eid=2-s2.0-77955413259&doi=10.1016%2fj.tet.2010.06.020&partnerID=40&md5=ebff60ba939c3a2a5c79c96f10ba25b7 | |
dc.subject | article | en |
dc.subject | priority journal | en |
dc.subject | unclassified drug | en |
dc.subject | chemical structure | en |
dc.subject | chemical reaction | en |
dc.subject | proton nuclear magnetic resonance | en |
dc.subject | anilide | en |
dc.subject | indole derivative | en |
dc.subject | methanol | en |
dc.subject | oxidation | en |
dc.subject | triphenylphosphine | en |
dc.subject | temperature measurement | en |
dc.subject | cyanide | en |
dc.subject | (2 cyano 5,6 dimethoxyindol 3 yl)iminotriphenylphosphorane | en |
dc.subject | (2 cyanoindol 3 yl)iminotriphenylphosphorane | en |
dc.subject | 2 (cyanomethylamino)benzonitrile | en |
dc.subject | 2 (cyanomethyleneamino) 4,5 dimethoxybenzonitrile | en |
dc.subject | 2 (cyanomethyleneamino)benzonitrile | en |
dc.subject | 2 cyano 4,5 dimethoxyphenylcyanothioformanilide | en |
dc.subject | 2 cyano cyanothioformanilide derivative | en |
dc.subject | 3 amino 4 methylindole 2 carbonitrile | en |
dc.subject | 3 amino 5 chloroindole 2 carbonitrile | en |
dc.subject | 3 amino 5 nitroindole 2 carbonitrile | en |
dc.subject | 3 amino 6 chloroindole 2 carbonitrile | en |
dc.subject | 3 amino 6 methoxyindole 2 carbonitrile | en |
dc.subject | 3 aminoindole 2 carbonitrile | en |
dc.subject | 3 aminoindole 2 carbonitrile derivative | en |
dc.subject | 4,5 dimethoxyanthranilonitrile | en |
dc.subject | 4,6,7 trimethoxyquinazoline 2 carbonitrile | en |
dc.subject | 6 chloro 4 methoxyquinazoline 2 carbonitrile | en |
dc.subject | 6,7 dimethoxyquinazoline 2 carbonitrile | en |
dc.subject | anthranilonitrile | en |
dc.subject | benzonitrile | en |
dc.subject | n (2 cyano 5 nitroindol 3 yl)iminotriphenylphosphorane | en |
dc.subject | n (2 cyanophenyl)formamide | en |
dc.subject | toluenesulfonic acid | en |
dc.subject | toluenesulfonic acid derivative | en |
dc.title | The conversion of 2-cyano cyanothioformanilides into 3-aminoindole-2- carbonitriles using triphenylphosphine | en |
dc.type | info:eu-repo/semantics/article | |
dc.identifier.doi | 10.1016/j.tet.2010.06.020 | |
dc.description.volume | 66 | |
dc.description.issue | 32 | |
dc.description.startingpage | 6032 | |
dc.description.endingpage | 6039 | |
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 :5</p> | en |
dc.source.abbreviation | Tetrahedron | en |
dc.contributor.orcid | Koutentis, Panayiotis Andreas [0000-0002-4652-7567] | |
dc.gnosis.orcid | 0000-0002-4652-7567 | |