186
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Revisit to the Reaction of O-Phenylene Diamine with Thiosemicarbazide to Give Benzimidazole-2-Thione Rather than Benzotriazine-2-Thione and its Glycosylation

, , &
Pages 698-706 | Received 28 May 2010, Accepted 11 Jun 2010, Published online: 11 Aug 2010

REFERENCES

  • Varki , A. 1993 . Biological roles of oligosaccharides: all of the theories are correct . Glycobiology , 3 ( 2 ) : 97 – 130 .
  • Bertozzi , C. R. and Kiessling , L. L. 2001 . Chemical glycobiology . Science , 291 : 2357 – 2364 .
  • Thibodeaux , C. J. , Melançon , C. E. and Liu , H. 2007 . Unusual sugar biosynthesis and natural product glycodiversification . Nature , 446 : 1008 – 1016 .
  • Ritchie , G. E. , Moffatt , B. E. , Sim , R. B. , Morgan , B. P. , Dwek , R. A. and Rudd , P. M. 2002 . Glycosylation and the complement system . Chem. Rev. , 102 : 305 – 320 .
  • Toshima , K. and Tatsuta , K. 1993 . Recent progress in O-glycosylation methods and its application to natural products synthesis . Chem. Rev. , 93 : 1503 – 1531 .
  • Davis , B. G. 2000 . Recent developments in oligosaccharide synthesis . J. Chem. Soc. Perkin Trans. 1 , 14 : 2137 – 2160 .
  • Schmidt , R. R. and Kinzy , W. 1994 . Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method . Adv. Carbohydr. Chem. Biochem. , 50 : 21 – 123 .
  • Bongat , A. F.G. and Demchenko , A. V. 2007 . Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars . Carbohydr. Res. , 342 : 374 – 406 .
  • Bongat , A. F.G. , Kamat , M. N. and Demchenko , A. V. 2007 . Chemoselective synthesis of oligosaccharides of 2-deoxy-2-aminosugars . J. Org. Chem. , 72 : 1480 – 1483 .
  • El Ashry , E. S.H. , Rashed , N. and Ibrahim , E. S.I. 2005 . Strategies of synthetic methodology for constructing β-mannosidic linkage . Curr. Org. Syn. , 2 : 175 – 213 .
  • El-Ashry , E. S.H. and Aly , M. R.E. 2007 . Synthesis and biological relevance of N-acetylglucoseamine-containing oligosaccharides . Pure Appl. Chem. , 79 : 2229 – 2242 .
  • El Ashry , E. S.H. , Rashed , N. and Ibrahim , E. I. 2008 . Challenges in the stereocontrolled syntheses of β-rhamnosides . Tetrahedron , 64 : 10631 – 10648 .
  • El Ashry , E. S.H. , Awad , L. F. and Atta , A. I. 2006 . Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry . Tetrahedron , 62 : 2943 – 2998 .
  • Defaye , J. and Gelas , J. 1991 . Studies in Natural Products Chemistry; Atta-ur-Rahman , Vol. 8E , 315 Amsterdam : Elsevier .
  • El Ashry , E. S.H. , Awad , L. F. , Abdel Hamid , H. M. and Atta , A. I. 2006 . Microwave Irradiation for Accelerating the Synthesis of Thioglycosides . Synthetic Commun. , 36 : 2769 – 2785 .
  • El Ashry , E. S.H. , Rashed , N. and Shobier , A. H. 2000 . Glycosidase inhbitors and their chemotherapeutic value, part 1 . Pharmzie , 55 : 251 – 262 .
  • El Ashry , E. S.H. , Rashed , N. and Shobier , A. H. 2000 . Glycosidase inhbitors and their chemotherapeutic value, part 2 . Pharmzie , 55 : 331 – 348 .
  • El Ashry , E. S.H. , Rashed , N. and Shobier , A. H. 2000 . Glycosidase inhbitors and their chemotherapeutic value, part 3 . Pharmzie , 55 : 403 – 415 .
  • El Ashry , E. S.H. , Kassem , A. A. , Abdel-Hamid , H. M. , Louis , F. , Khattab , Sh.A.N. and Aouad , M. R. 2009 . Regioselectivity in the glycosylation of 5-(3-chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole-3-thiol . Carbohydr. Res. , 344 : 725 – 733 .
  • Rezki , N. , Rashed , N. , Awad , L. F. , Ramadan , E. , Abdel-Maggeed , S. M. and El Ashry , E. S.H. 2009 . Regio- and selective synthesis of thioglycosides derivatives from 4,5-diphenyl- and 3,4,5-triphenyl-imidazole-2-thione . Phosphorus Sulfur Silicon , 184 : 1759 – 1767 .
  • Bala , S. , Sachdeva , M. L. , Handa , R. N. and Pujari , H. K. 1980 . Heterocyclic systems containing bridgehead nitrogen atom. Part XXXVII. Reaction of mercapto-as-benzotriazines with halogeno acetic acid α-halogenoketones and alkyl halides . Heterocycles , 14 : 149 – 157 .
  • Heravi , M. M. , Aghapoor , K. , Nooshabadi , M. A. and Mojtahedi , M. M. 1997 . Regioselective Annelation of 3-(prop-2-ynylsulfanyl)-1,2,4-benzotriazine to thiazolo[2,3-c][1,2,4]benzotriazine . Monatsh. Chem. , 128 : 1143 – 1147 .
  • Heravi , M. M. , Tavalaie , Z. and Sabzevari , O. 1998 . Synthesis of a novel heterocyclic system: Oxazolo[2,3-c][1,2,4]benzotriazine . Indian J. Chem. , 37B : 585 – 586 . Chem. Abstr. 1998, 260362y
  • Heravi , M. M. , Oskooie , H. A. , Beheshtiha , Y. Sh. , Nami , N. and Ghoresishi , S. 1998 . Synthesis and characterization of a new heterocyclic system: 1,3-thiazino[1,2-c][1,2,4]benzotriazines . Indian J. Heterocyclic Chem. , 7 : 303 – 304 .
  • Heravi , M. M. , Aghapoor , K. , Noorshabadi , M. A. , Mojtahedi , M. M. and Oskooie , H. A. 1999 . Selective cyclization and isomerization of a 3-propargylthio-1,2,4-benzotriazine to a thiazolo[2,3-c][1,2,4] benzotriazine . J. Sci. I. R. Iran , 10 : 31 – 34 . Chem. Abstr. 1999, 271859h
  • Hervai , M. M. , Rahimizadeh , M. , Iravani , E. and Ghassemzadeh , M. 2003 . Synthesis of bicyclic compounds derived from 1,2,4-benzotriazines . Phosphorus, Sulfur Silicon , 178 : 797 – 802 .
  • Bakavoli , M. , Seresht , E. R. and Rahimizadeh , M. 2006 . Reinvestigation of o-phenylenediamine thermal cyclocondensation with thiosemicarbazide . Heterocyclic Commun. , 12 : 273 – 274 .
  • Van Allan , J. A. and Deacon , B. D. 1963 . 2-Mercatobenzimidazole . Org. Synth., Coll. , 4 : 569 – 570 .
  • Zinner , H. and Peseke , K. 1969 . Benzazoles. XXV. Glucosidation of benzimidazolethione . J. Prakt. Chem. , 311 : 997 – 1012 .
  • Hwu , J. R. , Singha , R. , Hong , S. C. , Chang , Y. H. , Das , A. R. , Vliegen , I. , Clercq , E. D. and Neyts , J. 2008 . Synthesis of new benzimidazole-coumarin conjugates as anti-hepatitis C virus agents . Antiviral Research , 77 : 157 – 162 .

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.