56043-01-7Relevant articles and documents
The conversion of 2-cyano cyanothioformanilides into 3-aminoindole-2- carbonitriles using triphenylphosphine
Koutentis, Panayiotis A.,Michaelidou, Sophia S.
scheme or table, p. 6032 - 6039 (2010/09/11)
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.
Design, synthesis, and evaluation of potential GAR and AICAR transformylase inhibitors
Boger, Dale L.,Kochanny, Monica J.,Cai, Hui,Wyatt, Diane,Kitos, Paul A.,Warren,Ramcharan,Gooljarsingh, Lata T.,Benkovic, Stephen J.
, p. 643 - 659 (2007/10/03)
The synthesis and evaluation of 1 4 as potential inhibitors of GAR Tfase and AICAR Tfase are detailed. Copyright (C) 1998 Elsevier Science Ltd.
EXLUSIVE ORTHO CYANATION AND ALKYLTHIOCARBONYLATION OF ANILINES AND PHENOLS USING BORON TRICHLORIDE
Adachi, Makoto,Sugasawa, Tsutomu
, p. 71 - 84 (2007/10/02)
Use of boron trichloride with or without an aditional Lewis acid makes possible a one-step synthesis of 2-cyano and 2-alkylthiocarbonyl anilines and phenols.