1,3-Dipolar Cycloaddition with the 5,7-Dimethyl-1,2-diazepine

Gas-Phase Infrared and ab Initio Study of the Unstable CF3CNO Molecule and Its Stable Furoxan Ring Dimer

“…Trifluoroacetonitrile N-oxide, CF 3 CNO (1), is often used in [2 + 3] cycloaddition reactions where five-membered heterocycles, for example, oxazoles, oxazolines, isoxazoles, and isoxazolines, including Diels-Alder adducts, can be prepared. [6][7][8][9][10][11][12] Recently, 1 has proven to be of interest in medical applications, acting as a reagent for preparing tachykinin receptor antagonists 13 as well as in the production of herbicides, pesticides, and insecticides. 14 In most cases, 1 is generated as a reactive dipolarophile in solution from Br-or Cl-oximes, specifically trifluoroacetohydroximoyl bromide and chloride, respectively, since it has been stated 6 to be unstable in solution "even at a temperature below -20°".…”

Highly Regio‐ and Diastereoselective 1,3‐Dipolar Cycloaddition of Nitrile Oxides to 2,4‐Dimethyl‐3H‐1,5‐Benzodiazepines: Synthesis of Bis[1,2,4‐Oxadiazolo][1,5]Benzodiazepine Derivatives

“…[1,2] In this context, our research team is interested in the synthesis of heterocyclic compounds from 1,2-diazepines, [3] 1,4-diazepines, [4] 1,2,4-triazepines, [5] 1,4-benzodiazepines, [6,7] 1,5-benzodiazepines, [8 -11] and 1,3,4-benzotriazepines [12] via the 1,3-dipolar cycloaddition reactions. In this paper, we report a one-step synthesis of new heterocyclic systems by 1,3-dipolar cycloaddition of nitrile oxides on the 2,4-dimethyl-3H-1,5-benzodiazepines 1a-c. [13] It is noteworthy that according to the substituent in C-7 of 1, the two dipolarophile sites are chemically equivalent (R¼H) or different (R¼Me, Cl).…”

Stéréochimie du 1,7-bis(4-chlorophényl)-3a,4a,10-triméthyl-3a,4a,8,13-tétrahydro-4H-bis[1,2,4-oxadiazolo][4,5-a:5′,4′-d][1,5]benzodiazépine

“…De plus, il a e  te  montre  que l'introduction de nouveaux he  te  rocycles pentagonaux sur l'he  te  rocycle diaze  pinique accroõ Ãt notablement l'activite  biologique de la mole  cule (Hester et al, 1970). Dans le but d'e  largir les travaux de notre e  quipe de recherche en se  rie des 1,2,4-triaze  pines (El Messaoudi et al, 1994;Toledano et al, 1996), 1,4-benzodiaze  pines (Benelbaghdadi et al, 1997) et 1,5-benzodiaze  pines (Baouid et al, 1996;Essaber et al, 1998;Aatif et al, 2000;El Hazazi et al, 2000, nous nous sommes inte  resse  s a Á la synthe Á se de nouveaux syste Á mes he  te  rocycliques ayant des structures homologues a Á des mole  cules biologiquement actives de  rive  s de la 2,4,7-trime  thyl-3H-1,5-benzodiaze  pine.…”