39785-48-3Relevant academic research and scientific papers
Novel 6-substituted benzothiazol-2-yl indolo[1,2-c]quinazolines and benzimidazo[1,2-c]quinazolines
Frère, Stéphane,Thiéry, Valérie,Bailly, Christian,Besson, Thierry
, p. 773 - 779 (2007/10/03)
The synthetic route to and a preliminary biological evaluation of novel indolo[1,2-c]quinazolines (8) and benzimidazo[1,2-c]quinazolines (9) are described. The products were obtained by condensation of the appropriate diamines (e.g. 2-(2-aminophenyl)indol
Eco-Friendly Microwave-Assisted Scaleable Synthesis of 2-Cyanobenzothiazoles via N-Arylimino-1,2,3-dithiazoles
Frere, Stephane,Thiery, Valerie,Besson, Thierry
, p. 3795 - 3804 (2007/10/03)
The cyclization procedure of N-aryl iminodithiazoles into 2-cyanobenzothiazoles was re-investigated with the aim to develop original and environmentally friendly procedures. In this article, the benefits associated with the microwave methodology are reported and the opportunity to use solvent-free procedures in order to scale up organic synthesis is studied. The result obtained show that the strong thermal effects due to graphite/microwaves interaction can be efficiently used for the synthesis of heterocyclic molecules for which traditional methods failed or are less attractive.
New route to 2-cyanobenzothiazoles via N-arylimino-1,2,3-dithiazoles
Besson, Thierry,Dozias, Marie-Joelle,Guillard, Jerome,Rees, Charles W.
, p. 3925 - 3926 (2007/10/03)
N-Arylimino-1,2,3-dithiazole derivatives 2 of 2-bromoanilines are converted in high yield into 2-cyanobenzothiazoles 3 by heating or, more rapidly, by focused microwave irradiation at atmospheric pressure, in pyridine containing cuprous iodide.
Conversion of imino-1,2,3-dithiazoles into 2-cyanobenzothiazoles, cyanoimidoyl chlorides and diatomic sulfur
English, Russell F.,Rakitin, Oleg A.,Rees, Charles W.,Vlasova, Olga G.
, p. 201 - 205 (2007/10/03)
Primary aromatic amines condense with 4,5-dichloro-1,2,3-dithiazolium chloride 1 to give high yields of the N-aryl imines 2 which on heating give 2-cyanobenzothiazoles 3, thus providing a simple two-step route to these heterocycles from the appropriate aniline. This thermolysis is favoured by electron donating substituents in the aniline ring, and retarded by electron withdrawing groups in favour of a second pathway in which both dithiazole sulfur atoms are lost to form cyanoimidoyl chlorides 4. This is the sole pathway when both aniline ortho positions are substituted. Analogous N-alkyl imines 5, prepared from the salt 1 and the bis(trimethylsilyl) derivatives of the amine, also decompose with loss of both sulfur atoms as singlet diatomic sulfur, S2. 4-Chloro-5-methylimino-5H-1,2,3-diathiazole 5a does this at 140-150°C and the S2 generated is intercepted with 2,3-diphenylbutadiene, 2,3-dimethylbutadiene and norbornene to give 16a, 16b and 17 respectively.
