169778-81-8Relevant articles and documents
The conversion of 2-(4-chloro-5H-1,2,3-dithiazolylideneamino)benzonitriles into 3-aminoindole-2-carbonitriles using triphenylphosphine
Michaelidou, Sophia S.,Koutentis, Panayiotis A.
experimental part, p. 8428 - 8433 (2009/12/26)
2-(4-Chloro-5H-1,2,3-dithiazolylideneamino)benzonitrile 1a reacts with triphenylphosphine (4 equiv) in the presence of water (2 equiv) to afford anthranilonitrile 2a, 3-aminoindole-2-carbonitrile 3a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 4a, tog
Antibacterial evaluation of novel N-arylimino-1,2,3-dithiazoles and N-arylcyanothioformamides
Cottenceau, Gilles,Besson, Thierry,Gautier, Valerie,Rees, Charles W.,Pons, Anne-Marie
, p. 529 - 532 (2007/10/03)
N-Aryl-1,2,3-dithiazoles 2 and the corresponding N-arylcyanothioformamides 3 have been synthesized via 4,5-dichloro-1,2,3-dithiazole derivatives, and their antibacterial activity measured; the dithiazoles are significantly active against Gram-positive bacteria.
1,2,3-Dithiazoles and new route to 3,1-benzoxazin-4-ones, 3,1-benzothiazin-4-ones and N-arylcyanothioformamides
Besson, Thierry,Emayan, Kumaraswamy,Rees, Charles W.
, p. 2097 - 2102 (2007/10/02)
Treatment of methyl anthranilate with 4,5-dichloro-1,2,3-dithiazolium chloride 3 in dichloromethane ar room temperature, followed by addition of pyridine, gave the amino derivative 7 (R = Me) as expected; anthranilic acid, however, gave 4-oxo-4H-3,1-benzoxazine-2-carbonitrile 5.If triphenylphosphine was added to the reaction mixture instead of pyridine, methyl anthranilate gave methyl N-(cyanothioformyl)anthranilate 12 (X = o-CO2Me) whilst anthranilic acid gave 4-oxo-4H-benzo-3,1-thiazine-2-carbonitrile 6.These differences are explained mechanistically.When anthranilic acid was treated with the dithiazolium chloride 3 without the addition of pyridine, the delicate imino derivative 4 of the free carboxylic acid could be isolated (60percent).This when heated in boiling toluene gave the benzoxazinone 5 quantitatively, and with triphenylphosphine at room temperature it gave the benzothiazinone 6 quantitatively.These reactions provide a good route to benzo substituted 2-cyanooxazinones and 2-cyanothiazinones from the corresponding anthranilic acids.With triphenylphosphine in dichloromethane at room temperature the imines 11 in general (i.e. without an o-CO2H group) gave the corresponding N-arylcyanothioformamides 12 in very high yields, thus providing a good route to these compounds in two mild steps from the corresponding anilines.
