Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 5
80
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of New Tetraheterocyclic Systems by the Mixed Condensation Reactions on [1,2,4]Triazolo[4,3‐a][1,5]benzodiazepines

, , &
Pages 573-578 | Received 28 Jul 2005, Published online: 16 Aug 2006

References

  • Pevarello , P. , Amici , R. , Colombo , M. and Varasi , M. 1993 . Nitrile oxide cycloaddition of non‐activated alkynes: a novel approach to the synthesis of neuroactive isoxazoles . J. Chem. Soc. Perkin Trans. 1 , 18 : 2151 – 2152 .
  • Bartsch , H. and Erker , T. 1988 . Studies on the chemistry of O,N‐ and S,N‐containing heterocycles. Synthesis of 1,5‐benzothiazepines with potential CNS activity . J. Heterocycl. Chem. , 25 : 1151 – 1154 .
  • Clovis , J. S. , Eckell , A. , Huisgen , R. and Sustamann , R. 1967 . 1,3‐Dipolar cycloaddition XXVIII: diphenylinitrilimine and aryl‐conjugated alkenes . Chem. Ber. , 100 : 1593 – 1600 .
  • Padwa , A. and Nahm , S. E. 1978 . Intramolecular 1,3‐dipolar cycloaddition reactions of alkenyl‐substituted nitrile imines . J. Org. Chem. , 43 : 1664 – 1668 .
  • Hemming , K. , Luheshi , A. B. N. , Redhouse , A. D. , Smalley , R. K. and Thompson , J. R. 1993 . 1,3‐Dipolar cycloadditions of 2‐ethoxy‐ and 2‐(ethylthio)‐1‐azetines with nitrile oxides, nitrile ylides and nitrilimines: an unexpected 1,2,4‐triazole formation . Tetrahedron , 49 : 4383 – 4408 .
  • Hasnaoui , A. , Baouid , A. and Lavergne , J.‐P. 1991 . Synthèse de 1,2,4‐triazolo[4,3‐d][1,4]diazépines et de 1,2,4‐oxodiazolo[4,5‐d][1,4]diazépines par cycloaddition dipolaire‐1,3 . J. Heterocycl. Chem. , 28 : 73 – 76 .
  • El Messaoudi , M. , Hasnaoui , A. and Lavergne , J.‐P. 1994 . 1,3‐Dipolar cycloaddition with the 5,7‐dimethyl‐1,2‐diazepine . Synth. Commun. , 24 : 513 – 520 .
  • Baouid , A. , Benharref , A. , Hasnaoui , A. and Lavergne , J.‐P. 1994 . Cycloaddition dipolaire‐1,3 des N‐aryl‐C‐éthoxycarbonylnitrilimines sur la 1‐méthyl‐5,7‐diphényl‐1,4‐diazépine et sur la 2‐méthyl‐4‐phényl‐1,5‐benzodiazépine . Bull. Soc. Chim. Belg. , 103 : 743 – 751 .
  • Toledano , P. , Ait Itto , My. Y. and Hasnaoui , A. 1996 . 3‐Mesityl‐6‐methylthio‐4‐phenyl‐6H‐isoxazolo[5,4‐e][1,2,4]triazepine . Acta Cryst. , C52 : 1230 – 1232 .
  • Benelbaghdadi , R. , Hasnaoui , A. and Lavergne , J.‐P. 1997 . Synthèse de nouveaux composés bihétérocycliques à partir du diazepam . Bull. Soc. Chim. Belg. , 106 : 813 – 815 .
  • Essaber , M. , Baouid , A. , Hasnaoui , A. , Benharref , A. and Lavergne , J.‐P. 1998 . Synthesis of new tri and tetraheterocyclic systems: 1,3‐Dipolar cycloaddition of nitrilimines on 2,7‐dimethyl‐4‐phenyl‐3H‐1,5‐benzodiazepine . Synth. Commun. , 28 : 4097 – 4104 .
  • Aatif , A. , Baouid , A. , Benharref , A. and Hasnaoui , A. 2000 . Synthesis of novel [1,2,4]triazolo[3,4‐d][1,5]benzodiazepinones derivatives by 1,3‐dipolar cycloaddition . Synth. Commun. , 30 : 2647 – 2659 .
  • Baouid , A. , Elhazazi , S. , Hasnaoui , A. , Compain , P. , Lavergne , J.‐P. and Huet , F. 2001 . Highly peri‐, regio‐ and diastereoselective 1,3‐dipolar cycloaddition of mesitonitrile oxide to 1,7‐dimethyl‐2,3‐dihydro‐1H‐1,4‐diazepines: unexpected one‐step formation of a new triheterocyclic framework . New J. Chem. , 25 : 1479 – 1481 .
  • Jalal , R. , El Messaoudi , M. , Hasnaoui , A. , Esseffar , M. , Selkti , M. , Lavergne , J.‐P. and Compain , P. 2002 . Synthesis of a novel heterocyclic ring system by way of highly regio and chemoselective 1,3‐dipolar cycloaddition of nitrilimines to 1,3,4‐benzotriazepin‐5‐one . New J. Chem. , 26 : 1545 – 1548 .
  • Elhazazi , S. , Baouid , A. , Hasnaoui , A. and Compain , P. 2003 . Peri and regioselestive synthesis of new heterocyclic compounds from 1,5‐benzodiazepine . Synth. Commun. , 33 : 19 – 27 .
  • Nabih , K. , Baouid , A. , Hasnaoui , A. , Selkti , M. and Compain , P. 2003 . 1,3‐Dipolar cycloaddition of nitrilimines to 2,4‐disubstituted‐3H‐1,5‐benzodiazepines: remarkable effect of C4‐substituent on diastereoselectivity . New J. Chem. , : 1644 – 1648 .
  • Huisgen , R. , Seidel , M. , Wallbillich , G. and Knupfer , H. 1962 . Diphenyl‐nitrilimin und seine 1.3‐dipolaren additionen an alkene und alkine . Tetrahedron , 17 : 3 – 29 .
  • Begtrup , M. , Elguero , J. , Faure , R. , Camps , P. , Estopa , C. , Ilavsky , D. , Fruchier , A. , Marzin , C. and Mendoza , J. 1988 . Effect of N‐Substituents on the 13C NMR Parameters of Azoles . Magn. Reson. Chem. , 26 : 134 – 151 .
  • Liu , K. C. , Shelton , B. R. and Howe , R. K. 1980 . A particularly convenient preparation of benzohydroximinoyl chlorides (nitrile oxides precursors) . J. Org. Chem. , 45 : 3916 – 3918 .
  • Grundmann , C. and Dean , J. M. 1965 . Nitrile Oxides. V. Stable aromatic nitrile oxides . J. Org. Chem. , 30 : 2809 – 2812 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.