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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 20
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Original Articles

Simple and New Protocol for the Synthesis of Novel (z)-3-Arylidenebenzothiazepin-4-ones Using Baylis–Hillman Derivatives

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Pages 3406-3413 | Received 22 Feb 2008, Published online: 29 Sep 2008

REFERENCES

  • Basavaiah , D. ; Venkateswara Rao , K. ; Reddy , R. J. The Baylis–Hilman reaction: A novel source of attraction, opportunities, and challenges in synthetic chemistry . Chem. Soc. Rev. 2007 , 36 , 1581 – 1588.
  • Basavaiah , D. ; Rao , A. J. ; Satyanarayana , T. Recent advances in the Baylis–Hilman reaction and applications . Chem. Rev. 2003 , 103 , 811 – 891.
  • Ciganek , E. Organic Reactions ; L. A. Paquette (Ed.); Wiley : New York , 1997 ; vol. 51 , pp. 201 – 350.
  • (a) Aroyan , C. E. ; Vasbinder , M. M. ; Miller , S. J. Dual catalyst control in the enantioselective intramolecular Morita–Baylis–Hillman reaction . Org. Lett. 2005 , 7 , 3849 – 3851 ; (b) Kabalka, G. W.; Dong, G.; Venkataiah, B.; Chen, C. Palladium-catalyzed cross-coupling of Baylis–Hillman acetate adducts with organosilanes. J. Org. Chem. 2005, 70, 9207–9210; (c) Krafft, M. E.; Haxell, T. F. N. Organomediated Morita–Baylis–Hillman cyclization reactions. J. Am. Chem. Soc. 2005, 127, 10168–10169.
  • (a) Basavaiah , D. ; Aravindu , K. The Baylis–Hillman acetates as a valuable source for one-pot multistep synthesis: A facile synthesis of functionalized tri-/tetracyclic frameworks containing azocine moiety . Org. Lett. 2007 , 9 , 2453 – 2456 ; (b) Basavaiah, D.; Mallikarjuna Reddy, R.; Kumaragurubaran, N.; Sharada, D. S. Applications of Baylis–Hillman chemistry: One-pot convenient synthesis of functionalized (1H)-quinol-2-ones and quinolines. Tetrahedron 2002, 58, 3693–3697; (c) Shanmugan, P.; Viswambharan, B.; Madhavan, S. Synthesis of novel functionalized 3-spiropyrrolizidine and 3-spiropyrrolidine oxindoles from Baylis–Hillman adducts of isatin and heteroaldehydes with azomethine ylides via [3 + 2]-cycloaddition. Org. Lett. 2007, 9, 4095–4098; (d) Dep, I.; Dadwal, M.; Mobin, S. M.; Namboothiri, I. N. N. Hydroxyalkylation of conjugated nitroalkenes with activated nonenolizable carbonyl compounds. Org. Lett. 2006, 8, 1201–1204.
  • Gonzalez , A. G. ; Silva , M. H. ; Padron , J. I. ; Leon , F. ; Reyes , E. ; Alvarez-mon , M. ; Pivel , J. P. ; Quintana , J. ; Estevez , F. ; Bermejo , J. Synthesis and antiproliferative activity of a new compound containing an α-methylene-γ-lactone group . J. Med. Chem. 2002 , 45 , 2358 – 2361.
  • Mergott , D. J. ; Frank , S. A. ; Roush , W. R. Application of the intramolecular vinylogous Morita–Baylis–Hillman reaction toward the synthesis of the spinosyn, a tricyclic nucleus . Org. Lett. 2002 , 4 , 3157 – 3160.
  • Trost , B. M. ; Thiel , O. R. ; Tsui , H. C. DYKAT of Baylis–Hillman adducts: Concise total synthesis of furaquinocin E . J. Am. Chem. Soc. 2002 , 124 , 11616 – 11617.
  • Loh , T. P. ; Cao , G. Q. ; Pei , J. Studies towards total synthesis of antillatoxin: Synthesis of C1–C11 fragment . Tetrahedron Lett. 1998 , 39 , 1457 – 1460.
  • (a) Amblard , M. ; Daffix , I. ; Bedos , P. ; Berge , G. ; Pruneau , D. ; Paquet , J. L. ; Luccarini , J. M. ; Belichard , P. ; Dodey , P. ; Martinez , J. Design and synthesis of potent bradykinin agonists containing a benzothiazepine moiety . J. Med. Chem. 1999 , 42 , 4185 – 4192 ; (b) Amblard, M.; Daffix, I.; Bergé, G.; Calmes, M.; Dodey, P.; Pruneau, D.; Paquet, J. L.; Luccarini, J. M.; Belichard, P.; Martinez, J. Synthesis and characterization of bradykinin B2 receptor agonists containing constrained dipeptidemimics. J. Med. Chem. 1999, 42, 4193–4201; (c) Robl, J. A.; Sun, C. Q.; Stevenson, J.; Ryono, D. E.; Simpkins, L. M.; Cimarusti, M. P.; Dejneka, T.; Slusarchyk, W. A.; Chao, S.; Stratton, L.; Misra, R. N.; Bednarz, M. S.; Asaad, M. M.; Cheung, H. S.; Abboa-Offei, B. E.; Smith, P. L.; Mathers, P. D.; Fox, M.; Schaeffer, T. R.; Seymour, A. A.; Trippodo, N. C. Dual metalloprotease inhibitors: Mercaptoacetyl-based fused heterocyclic dipeptide mimetics as inhibitors of angiotensin-converting enzyme and neutral endopeptidase. J. Med. Chem. 1997, 40, 1570–1577.
  • Boschelli , D. H. ; Connor , D. T. ; Kramer , J. B. ; Unangst , P. C. Method for treating inflammatory disease in humans. U.S. Patent 5,489,586, Dec. 12, 1994.
  • Watson , K. G. ; Fung , Y. M. ; Gredley , M. ; Bird , G. J. ; Jackson , W. R. ; Gountzos , H. ; Matthews , B. R. Asymmetric syntheses of (+)-diltiazem hydrochloride . J. Chem. Soc., Chem. Commun. 1990 , 1018 – 1019.
  • Schwartz , A. ; Madan , P. B. ; Mohacai , E. ; O'Brien , J. P. ; Todaro , L. J. ; Coffen , D. L. Enantioselective synthesis of calcium channel blockers of the diltiazem group . J. Org. Chem. 1992 , 57 , 851 – 856.
  • Lohray , B. B. ; Jayachandran , B. ; Bhushan , V. ; Nandanan , E. ; Ravindranathan , T. Anchimeric assisted unprecedented SNi-type cleavage of cyclic sulfite: Application in the synthesis of the calcium channel blocker diltiazem . J. Org. Chem. 1995 , 60 , 5983 – 5985.
  • Yamada , S. ; Mori , Y. ; Morimatsu , K. ; Ishizu , Y. ; Ozaki , Y. ; Yoshioka , R. ; Nakatani , T. ; Seko , H. Asymmetric reduction of a 1,5-benzothiazepine derivative with sodium borohydride-(S)-α-amino acids: An efficient synthesis of a key intermediate of diltiazem . J. Org. Chem. 1996 , 61 , 8586 – 8590.
  • Li , R. ; Farmer , S. P. ; Xie , M. ; Quilliam , M. A. ; Pleasance , S. ; Howlett , S. E. ; Yeung , P. K. F. Synthesis, characterization, and Ca2+ antagonistic activity of diltiazem metabolites . J. Med. Chem. 1992 , 35 , 3246 – 3253 .
  • Krapcho , J. ; Turk , C. F. Substituted 2,3-dihydro-1,5-benzothiazepin-4(5H)-one and related compounds, II: A new class of antidepressants . J. Med. Chem. 1966 , 9 , 191 – 195.
  • Basavaiah , D. ; Bakthadoss , M. ; Pandiaraju , S. A new protocol for the syntheses of (E)-3-benzylidenechroman-4-ones: A simple synthesis of the methyl ether of bonducellin . Chem. Commun. 1998 , 1639 – 1640.
  • (a) Basavaiah , D. ; Bakthadoss , M. ; Jayapal Reddy , G. The first intramolecular Friedel–Crafts reaction of Baylis–Hillman adducts: Synthesis of functionalized indene and indane derivatives . Synthesis 2001 , 6 , 919 – 923 ; (b) Basavaiah, D.; Bakthadoss, M.; Jayapal Reddy, G. Tandem construction of carbon–carbon and carbon–oxygen bonds in the Baylis–Hillman chemistry: Synthesis of functionalized dl-bis-allyl ethers. Synth. Commun. 2002, 32, 689–697.
  • Bakthadoss , M. ; Sivakumar , N. ; Sivakumar , G. ; Murugan , G. Highly regio- and stereoselective synthesis of tricyclic frameworks using Baylis–Hillman derivatives . Tetrahedron. Lett. 2008 , 49 , 820 – 823.

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