Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 3
230
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Utility of α-Oxoketene and α-Cyanoketene Thioacetals in Heterocyclic Syntheses: Synthesis of Some New Benzothiazepine Derivatives

Pages 331-340 | Received 10 Aug 2009, Published online: 13 Jan 2011

REFERENCES

  • (a) Mane , R. A. ; Ingle , D. B. Synthesis and biological activity of some new 1,5-benzothiazepines containing thiazole moiety . Ind. J. Chem., Sect. B 1982 , 21B , 973 ; (b) Attia , A. ; Abdel-salam , O. I. ; Abo-Ghalia , M. H. ; Amr , A. E. Chemical and biological reactivity of newly synthesized 2-chloro-6-ethoxy-4-acetylpyridines . Egypt. J. Chem. 1995 , 38 , 543 – 553 .
  • Reddy , R. J. ; Ashok , D. ; Sarma , P. N. Synthesis of 4,6-bis(2′-substituted-2′,3′-dihydro-1,5-benzothiazepin-4′-yl)resorcinols as potential antifeedants. Ind. J. Chem., Sect. B 1993, 32, 404–406.
  • Satyanarayana , K. ; Rao , M. N. A. Synthesis of 3-[4-[2,3-dihydro-2-(substitutedaryl)-1,5-benzothiazepin-4-yl]phenyl]sydnones as potential anti-inflammarory agents . Ind. J. Pharm. Sci. 1993 , 55 , 230 – 234 .
  • DeSarro , G. ; Chimirri , A. ; DeSarro , A. ; Gitto , R. ; Grasso , S. ; Zappala , M. 5H-[1,2,4]Oxadiazolo[5,4-d]benzothiazepines as anticonvulsant agents in DBA/2 mice . Eur. J. Med. Chem. 1995 , 30 ( 12 ), 925 – 929 .
  • Gronowitz , S. The Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives ; Wiley : New York , 1991 ; vol. 44 .
  • (a) Pinto , I. L. ; Jarvest , R. L. ; Serafinowska , H. T. The synthesis of 5-alkoxy and 5-amino substituted thiophenes . Tetrahedron Lett. 2000 , 41 ( 10 ), 1597 – 1600 ; (b) Luker , T. J. ; Beaton , H. G. ; Whiting , M. ; Mete , A. ; Cheshire , D. R. Palladium-catalysed amination of electron-deficient halothiophenes . Tetrahedron Lett. 2000 , 41 ( 40 ), 7731 – 7735 .
  • (a) Bohlmann , F. ; Zdero , C. ; Gronowitz , S. Thiophene and Its Derivatives ; John Wiley & Sons : New York , 1985 ; part 1 , p. 261 ; (b) Koike , K. ; Jia , Z. ; Nikaido , T. ; Liu , Y. ; Zhao , Y. ; Guo , D. Echinothiophene, a novel benzothiophene glycoside from the roots of Echinops grijissii. Org. Lett. 1999, 1(2), 197–198 .
  • (a) Kiess , H. Conjugated Conducting Polymers ; Springer : New York , 1992 ; vol. 102 ; (b) Roncali , J. Conjugated poly(thiophenes): Synthesis, functionalization, and applications. Chem. Rev. 1992, 92(4), 711–738 ; (c) Schopf , G. ; Kossmehl , G. Polythiophenes—Electrically conductive polymers. Adv. Polym. Sci. 1997, 129, 1 .
  • Watanabe , M. ; Yamamoto , T. ; Nishiyama , M. Synthesis of novel (bis) (diarylamino)thiophenes via palladium-catalysed reaction of (di)bromothiophenes . Chem. Commun. 2000 , 133 – 135 .
  • Katritzky , A. R. ; Odens , H. H. ; Zhang , S. Novel synthesis of 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones and 2H-1,4-benzothiazin-3(4H)-ones . J. Org. Chem. 2001 , 66 , 6792 .
  • Prakash , O. ; Kumar , A. ; Sadana , A. ; Prakash , R. ; Singh , S. P. ; Claramunt , R. M. ; Sanz , D. ; Alkorta , I. ; Elguero , J. Study of the synthesis of chalcone analogs of dehydroacetic acid and o-aminothiophenol: Synthesis and structure of 1,5-benzothiazepines and 1,4-benzothiazines . Tetrahedron 2005 , 61 , 6642 – 4451 .
  • Braun , R. U. ; Muller , T. J. One-pot synthesis of dihydrobenzo[b][1,4]thiazepines and diazepines via coupling isomerisation-cyclocondensation sequences . Tetrahedron 2004 , 60 ( 42 ), 9463 – 9469 .
  • Levai , A. Oxazepines and thiazepines, 41: Synthesis of 4-aryl-2,3-dihydro-2-styryl-1,5-benzothiazepines by the reaction of (E,E)-cinnamylidene-acetophenones with 2-aminothiophenol and their conversion into 2,2-disubstituted 3-acetyl-2,3-dihydrobezothiazoles . J. Heterocycl. Chem. 2004 , 41 , 399403 .
  • Karthikeyan , S. V. ; Peruma , S. A facile tandem protocol for the synthesis of the regioselective synthesis of novel thienobenzothiazepines . Tetrahedron Lett. 2007 , 48 ( 13 ), 2261 – 2265 .
  • El-Shafei , A. K. ; El-Saghier , A. M. M. ; Ahmed , E. A. Synthesis of some new spiro(pyrano-4,2′-benzoxazole) derivatives . Synthesis 1994 , 152 .
  • Farhat , M. F. ; El-Saghier , A. M. M. ; Makhlouf , M. A. ; Kreddan , K. M. ; Elmezoughi , A. B. Ketene-N,S-acetals in heterocyclic synthesis, part 1: Synthesis of N-phenyl-2-ylidene and 2,5-diylidene thiazolidinone derivatives . J. Sulfur Chem. 2007 , 28 ( 6 ), 563 – 572 .
  • El-Saraf , G. A. ; El-Sayed , A. M. ; El-Saghier , A. M. M. One-pot PTC synthesis of polyfused pyrazoles . Heteroatom 2003 , 14 ( 3 ), 211 – 217 .
  • Abdel-Ghany , H. A. ; El-Saghier , A. M. M. ; El-Sayed , A. M. A novel synthesis of heterocyclic compounds from α-oxoketene-S,S-acetal. Synth. Commun. 1996, 26(22), 4289–4297.
  • El-Saghier , A. M. M. ; Maihub , A. A. ; Al-Shirayda , H. A. A novel synthesis of imidazo[2,1-d][1,2,4]triazine and imidazo[2,1-d][1,2,5]triazepine derivatives via ketene-N,S-acetal . Synth. Commun. 1996 , 27 ( 14 ), 2433 – 2444 .
  • El-Sayed , A. M. ; Abdel-Ghany , H. A. ; El-Saghier , A. M. M. A novel synthesis of pyrano(2,3-c)-, 1,3-oxazino(2,3-b)-, 1,2,4-triazolo(3,4-b)-, oxazolo(2,3-b)-, furano(2,3-c), and 3-substituted-(1,5)-benzodiazepin-2-ones . Synth. Commun. 1999 , 29 ( 20 ), 3561 – 3572 .
  • El-Saghier , A. M. M. ; Farhat , M. F. ; Farhat , M. F. 1,4-Diazepines bearing thieno(2,3-b)thiophene and cyclohexene carboxylate moieties . Phosphorus, Sulfur Silicon Relat. Elem. 2006 , 181 ( 7 ), 1569 – 1582 .

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.