853995-64-9Relevant academic research and scientific papers
Microwave-assisted regioselective N-alkylation of cyclic amidines
Pereira, Maria de Fatima,Thiéry, Valérie,Besson, Thierry
, p. 7657 - 7659 (2007)
A simple and efficient methodology for regioselective alkylation of exocyclic nitrogen of cyclic amidines was developed by microwave-assisted heating in the presence of amines. Novel N-alkylated 3,4-dihydropyrazino[2,1-b]quinazolin-6-ones were prepared in
A rapid and convenient synthesis of novel 1-imino-2,3-dihydro-1H- pyrazino[2,1,-b]quinazolin-5-ones
Pereira, Maria De Fatima,Alexandre, Fran?ois René,Thiéry, Valérie,Besson, Thierry
, p. 3097 - 3099 (2007/10/03)
Exploring original approaches for the synthesis of therapeutic agents having a quinazoline part, we discovered that novel 3,4-dihydro-2H-pyrazino[2,1, -b]quinazolines (3) may be rapidly and easily obtained via the chemistry of 4,5-dichloro-1,2,3-dithiazol
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.
Antimicrobial evaluation of 3,1-benzoxazin-4-ones, 3,1-benzothiazin-4-ones, 4-alkoxyquinazolin-2-carbonitriles and N-arylimino-1,2,3-dithiazoles
Besson, Thierry,Rees, Charles W.,Cottenceau, Gilles,Pons, Anne-Marie
, p. 2343 - 2348 (2007/10/03)
Novel 3,1-benzoxazinones, 3,1-benzothiazinones and 4-alkoxyquinazolines have been synthesized via N-aryl-1,2,3-dithiazoles derivatives. The antibacterial and antifungal activity of these compounds were measured; the dithiazoles are significantly active against fungi.
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.
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.
