169778-78-3Relevant academic research and scientific papers
Synthesis of novel 2,3-substituted quinazolin-4-ones by condensation of alkyl or aromatic diamines with 5-(N-arylimino)-4-chloro-5H-1,2,3-dithiazoles
de Fatima Pereira, Maria,Thiéry, Valérie,Besson, Thierry
, p. 847 - 854 (2007/10/03)
The work described in this paper is a further example of the utility of Appel's salt in the conception of novel heterocyclic rings. We confirmed that primary alkyldiamines may react easily with the methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-anthrani
Reactions of Isocyanates with Methyl N-(Cyanothioformyl)anthranilate
Deck,Papadopoulos,Smith
, p. 885 - 893 (2007/10/03)
The triethylamine-catalyzed reactions of methyl N-(cyanothioformyl)anthranilate (1) with isocyanates result in cyclization involving the cyano group to form methyl 2-(4-imino-2-oxo-3-substituted-5-thioxoimidazolidin-1-yl)benzoates (4). Ring closure at the ester carbonyl to form 3-aryl-3,4-dihydro-4-oxoquinazoline-2-carbonitriles (8) is observed when the S-methyl derivative of 1 is allowed to react with aromatic amines.
A short synthesis of quinazolinocarboline alkaloids rutaecarpine, hortiacine, euxylophoricine A and euxylophoricine D from methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates
Mohanta, Pramod K.,Kim, Kyongtae
, p. 3993 - 3996 (2007/10/03)
Reactions of methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates with tryptamine at room temperature produced 2-cyano-3-[2-(indol-3-yl)ethyl]-4(3H)-quinazolinones, which underwent cyclization on heating with TFAA/HCl(g) to afford quinazolinocarboline alkaloids rutaecarpine (1a), hortiacine (1b), euxylophoricine A (1c) and euxylophoricine D (1d) in excellent yields.
A Facile Synthesis of 3-Substituted 2-Cyanoqmnazolin-4(3H)-ones and 3-Alkyl-2-cyanothieno[3,2-d]pyrimidin-4(3H)-ones via 1,2,3-Dithiazoles
Lee, Hyi-Seung,Chang, Yong-Goo,Kim, Kyongtae
, p. 659 - 668 (2007/10/03)
The reaction of methyl anthranilate with 4,5-dichloro-l,2,3-dithiazolium chloride (Appel's salt) in the presence of pyridine (2 equivalents) in dichloromethane at room temperature gave methyl N-(4-chloro-5H-l,2,3-dithiazol-5-ylidene)anthranilate (3a) (50% yield), which reacted with sterically less hindered primary alkylamines to give directly 3-alkyl-2-cyanoquinazolin-4(3H)-ones 5 in moderate to good yields. With tertbutylamine, N-(2-methoxycarbonylphenyl)iminocyanomethyl N-(tert-butyl) disulfide 7 and methyl 2-(N-cyanothioformamido)anthranilate (8) were isolated in 33% and 59% yields, respectively. The cyano group of quinazoline 5a (R = CH3) is readily displaced by various nucleophiles to give 2-substituted quinazolinones 11-19, which indicates that compounds 5 can be utilized as starting materials for the synthesis of new 2-substituted quinazolines. Similarly 3-alkyl-2-cyanothieno[3,2,-d]pyrimidin-4(3H)-ones 22 were prepared from methyl 3-[N-(4-chloro-5H-l,2,3-dithiazol-5-ylidene)]-2-thiophencarboxylate (21) in moderate to good yields.
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.
3,1-Benzoxazin-4-ones, 3,1-Benzothiazin-4-ones and N-Arylcyanothioformamides
Besson, Thierry,Emayan, Kumaraswamy,Rees, Charles W.
, p. 1419 - 1420 (2007/10/02)
Anthranilic acid and 4,5-dichloro-1,2,3-dithiazolium chloride 1 give the delicate dithiazoloimino carboxylic acid 8 which on mild thermolysis gives 2-cyano-3,1-benzoxazin-4-one 6 and with triphenylphosphine gives 2-cyano-3,1-benzothiazin-4-one 7, both quantitatively; in general N-aryliminodithiazoles 2 with triphenylphosphine give the corresponding cyanothioformanilides 3, providing a route to these compounds from anilines in two mild steps.
