NaCl as a Novel and Green Catalyst for the Synthesis of Biodynamic Spiro Heterocycles in Water Under Sonication

REFERENCES

• Anastas , P. T. ; Warner , J. C. Green chemistry: Theory and practice; Oxford University Press : New York , 1988 .
   Google Scholar
• Matlack , A. S. Introduction to Green Chemistry; Marcel Dekker: New York , 2001 .
   Google Scholar
• Lancester , M. Green Chemistry: An Introductory Text; Royal Society of Chemistry : Cambridge , 2002.
   Google Scholar
• Khosropour , A. R. Ultrasound-promoted greener synthesis of 2,4,5-trisubstituted imidazoles catalyzed by Zr(acac)4 under ambient conditions . Ultrason. Sonochem. 2008 , 15 , 659 – 664 .
   PubMed Web of Science ®Google Scholar
• Wang , S. X. ; Li , Z. Y. ; Zhang , J. C. ; Li , J. T. The solvent-free synthesis of 1,4-dihydropyridines under ultrasound irradiation without catalyst . Ultrason. Sonochem. 2008 , 15 , 677 – 680 .
   PubMed Web of Science ®Google Scholar
• Chandra , A. ; Fokin , V. V. Organic synthesis “on water.” Chem. Rev. 2009 , 109 , 725 – 748 .
   PubMed Web of Science ®Google Scholar
• Trost , B. M. ; Brennan , M. K. Asymmetric syntheses of oxindole and indole spirocyclic alkaloid natural products . Synthesis 2009 , 18 , 3003 – 3025 .
   Web of Science ®Google Scholar
• Galliford , C. V. ; Scheidt , K. A. Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents . Angew. Chem. Int. Ed. 2007 , 46 , 8748 – 8758 .
   PubMed Web of Science ®Google Scholar
• Marti , C. ; Carreira , E. M. Construction of spiro[pyrrolidine-3,3′-oxindoles]—Recent applications to the synthesis of oxindole alkaloids . Eur. J. Org. Chem. 2003 , 63 , 2209 – 2219 .
   Web of Science ®Google Scholar
• Wong , W. H. ; Lim , P. B. ; Chuah , C. H. Oxindole alkaloids from Alstonia Macrophylla . Phytochemistry 1996 , 41 , 313 – 315 .
   Web of Science ®Google Scholar
• Garnick , R. L. ; Lequesne , P. W. Biomimetic transformations among monomeric macroline-related indole alkaloids . J. Am. Chem. Soc. 1978 , 100 , 4213 – 4219 .
   Web of Science ®Google Scholar
• Dideberg , O. ; Brasseur , J. L. ; Dupont , L. ; Campsteyn , H. ; Vermeire , M. ; Angenot , L. Structure cristalline et moléculaire d'un nouvel alcalöide bisindolique: Complexe moléculaire 1:2 strychnofoline-ethanol (C30H34N4O2 · 2C2H6O) . Acta Crystallogr. Sect. B 1977 , 33 , 1796 – 1801 .
   Google Scholar
• Sakai , S. ; Aimi , N. ; Yamaguchi , K. ; Yamanaka , E. ; Haginiwa , J. Gardneria Alkaloids, part 13: Structure of gardmultine and demethoxygardmultine; bis- type indole alkaloids of Gardneria multiflora Makino . J. Chem. Soc., Perkin Trans. 1 1982 , 1257 – 1262 .
   Google Scholar
• Abdelrazek , F. M. ; Metz , P. ; Kataeva , O. ; Jager , A. ; El-Mahrouky , S. F. Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives . Arch. Pharm. Chem. Life Sci. 2007 , 340 , 543 – 548 .
   PubMed Web of Science ®Google Scholar
• Patel , H. D. ; Mistry , B. D. ; Desai , K. R. Synthesis and antimicrobial activity of pyrano[2,3-c]pyrazole derivatives . Oriental. J. Chem. 2003 , 19 , 497 – 498 .
   Google Scholar
• Abdallah , N. A. ; Zaki , M. E. A. Synthesis and pharmacological evaluation of some pyrano[2,3-c]pyrazole derivatives of analgesic and antiinflamatory profiles . Acta Pharm. 1999 , 49 , 159 – 170 .
   Google Scholar
• Gerencser , J. ; Dorman , G. ; Darvas , F. Meldrum's acid in multicomponent reactions: Applications to combinatorial and diversity-oriented synthesis . QSAR Comb. Sci. 2006 , 439 – 448 .
   Google Scholar
• Ramon , D. J. ; Yus , M. Asymmetric multicomponent reactions (AMCRs): The new frontier . Angew. Chem. Int. Ed. 2005 , 44 , 1602 – 1634 .
   PubMed Web of Science ®Google Scholar
• Dandia , A. ; Arya , K. ; Sati , M. ; Sharma , R. Facile microwave-assisted one-pot Solid-phase synthesis of spiro[3H-indole-3,4′-pyrazolo[3,4-b]pyridines] . Heterocycl. Commun. 2003 , 9 , 415 – 420 .
   Web of Science ®Google Scholar
• Dandia , A. ; Singh , R. ; Sachdeva , H. ; Gupta , R. ; Paul , S. Microwave-promoted and improved thermal synthesis of spiro-[indole pyranobenzopyrans] and spiro[indole-pyranoimidazoles] . J. Chin. Chem. Soc. 2003 , 50 , 273 – 278 .
   Web of Science ®Google Scholar
• Joshi , K. C. ; Dandia , A. ; Baweja , S. ; Joshi , A. Studies in spiroheterocycles, part XVII: Synthesis of novel fluorine containing spiro[indole pyranobenzopyran] and spiro[indenopyran-indole]derivatives . J. Heterocycl. Chem. 1989 , 26 , 1097 – 1099 .
   Web of Science ®Google Scholar
• Zhu , S. L. ; Ji , S. J. ; Zhang , Y. A simple and clean procedure for three-component synthesis of spirooxindoles in aqueous medium. Tetrahedron 2007, 63, 9365–9372.
   Web of Science ®Google Scholar
• Shanthi , G. ; Subbulakshmi , G. ; Perumal , P. T. A new InCl3-catalyzed, facile, and efficient method for the synthesis of spirooxindoles under conventional and solvent-free microwave conditions . Tetrahedron 2007 , 63 , 2057 – 2063 .
   Web of Science ®Google Scholar
• Elinson , M. N. ; Dorofeev , A. S. ; Miloserdov , F. M. ; Nikishin , G. I. Electrocatalytic multicomponent assembling of isatins,3-methyl-2-pyrazolin-5-ones and malononitrile: Facile and convenient way to functionalized spirocyclic [indole-3,4′-pyrano[2,3-c]pyrazole]system . Mol. Divers. 2009 , 13 , 47 – 52 .
   PubMed Web of Science ®Google Scholar
• Elinson , M. N. ; Ilovaisky , A. L. ; Dorofeev , A. S. ; Merkulova , V. M. ; Stepanov , N. O. ; Miloserdov , F. M. ; Ogibin , Y. N. ; Nikishin , G. I. Electrocatalytic multicomponent transformation of cyclic 1, 3-diketones, isatins, and malononitrile: Facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system . Tetrahedron 2007 , 63 , 10543 – 10548 .
   Web of Science ®Google Scholar
• Dandia , A. ; Singh , R. ; Bhaskaran , S. Ultrasound-promoted greener synthesis of spiro[indole-3,5′-[1,3]oxathiolanes in water . Ultrason. Sonochem. 2010 , 17 , 399 – 402 .
   PubMed Web of Science ®Google Scholar
• Dandia , A. ; Arya , K. The expedient synthesis of 1,5-benzothiazepines as a family of cytotoxic drugs . Bioorg. Med. Chem. Lett. 2008 , 18 , 114 – 119 .
   PubMed Web of Science ®Google Scholar