Versatility of Alternative Reaction Media: Water-Mediated Domino and Green Chemical Synthesis of Pyrimido[1,2-a]benzimidazole Under Nonconventional Conditions

REFERENCES

• Kubo , K. ; Inada , Y. ; Kohara , Y. ; Sugiura , Y. ; Ojima , M. ; Itoh , K. ; Yoshiyasu , F. ; Kohei , N. ; Nakat , T. Nonpeptide angiotensin I1 receptor antagonists: Synthesis and biological activity of benzimidazoles . J. Med. Chem. 1993 , 36 , 1772 – 1784 .
   PubMed Web of Science ®Google Scholar
• Bartlett , M. S. ; Edlind , T. D. ; Durkin , M. M. ; Shaw , M. M. ; Queener , S. F. ; Smith , J. W. Antimicrotubule benzimidazoles inhibit in vitro growth of Pneumocystis carinii . Antimicrob. Agents. Chemother. 1992 , 36 , 779 – 782 .
   PubMed Web of Science ®Google Scholar
• Paramashivappa , R. ; Phani Kumar , P. ; Subba Rao , P. V. ; Rao , S. A. Design, synthesis, and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors . Bioorg. Med. Chem. 2003 , 13 , 657 – 660 .
   Web of Science ®Google Scholar
• Dhage , A. N. ; Jashi , N. S. ; Wadokar , S. G. ; Kasture , A. V. Antimicrobial and local anthesthetic activity of some benzimidazoles . Indian Drugs 1986 , 23 , 601 ; Chem. Abstr. 1987 , 106 , 168513 .
   Google Scholar
• Elnima , E. I. ; Zubair , M. U. ; Al-Badr , A. A. Antibacterial and antifungal activities of benzimidazole and benzoxazole derivatives . Antimicrob Agents Chemother. 1981 , 19 , 29 – 32 .
   PubMed Web of Science ®Google Scholar
• Ramalingan , C. ; Balasubramanian , S. ; Kabilan , S. A convenient synthesis of novel 1-[2-(benzimidazol-2-yl)ethoxy]-2,6-diarylpiperidin-4-ones . Synth. Commun. 2004 , 34 ( 6 ), 1105 – 1116 .
   Web of Science ®Google Scholar
• (a) De Araujo , J. E. ; Huston , J. P. ; Brandao , M. Opposite effects of substance P fragment C (anxiogenic) and N (anxiolutic) injected into doal pariaqueductal gray . Eur. J. Pharmaco. 2001 , 432 ( 1 ), 43 – 51 . (b) Wonda, N.; Michal, Z. Synthesis and immunotropic activity of some 2-aminobenzimdazoles. Archiv der pharmazie 1999, 337, 249–253; (c) Trapani, G.; Farnco, M.; Latrofa, A.; Genchi, G.; Iacobazzi, V. Synthesis and benzodiazepine receptor binding of some imidazo-pyrimido[2,1-b] benzoxazoles and pyrimido[1,2-a]benzimidazoles. Eur. J. Med. Chem. 1997, 32(1), 83–90 .
   PubMed Web of Science ®Google Scholar
• (a) Sheldon , R. A. Green solvents for sustainable organic synthesis: State of the art . Green Chem. 2005 , 7 , 267 – 278 . (b) Manabe, K.; Limura, S.; Sun, X.-M.; Kobyashi, S. Dehydration reactions in water: Brønsted acid surfactant-combined catalyst for ester, ether, thioether, and dithioacetal formation in water. J. Am. Chem. Soc. 2002, 124, 11971–11978, and references cited therein .
   Web of Science ®Google Scholar
• (a) Li , C.-J. ; Chan , T.-H. Organic Reactions in Aqueous Media ; New York : Wiley Interscience , 1997 ; (b) Lindstrom, U. M. Stereoselective organic reactions in water. Chem. Rev. 2002, 102, 2751–2772; (d) Li, C.-J. Organic reactions in aqueous media with a focus on C-C bond formations. Chem. Rev. 2005, 105, 3095–3165 .
   Google Scholar
• (a) Loupy , A. Microwaves in Organic Synthesis ; Wiley-VCH : Weinheim , 2006; (b) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, 2005.
   Google Scholar
• Pang , Y. ; Song , G. ; Dou , R. Surface cleaning under combined microwave and ultrasound irradiation: Flash synthesis of 4H-pyrano[2,3-c]pyrazoles in aqueous media . Green Chem. 2006 , 8 , 573 – 575 .
   Web of Science ®Google Scholar
• Armstrong , R. W. ; Combs , A. P. ; Tempest , P. A. ; Brown , S. D. ; Keating , T. A. Multiple-component condensation strategies for combinatorial library synthesis . Acc. Chem. Res. 1996 , 29 , 123 – 131 ; (b) Dax, S. L.; McNally, J. J.; Yougman, M. A. Multi-component methodologies in solid-phase organic synthesis. Curr. Med. Chem. 1999, 6, 255–270 .
   Web of Science ®Google Scholar
• (a) Krasovsky , A. L. ; Hartulyari , A. S. ; Nenajdenko , V. G. ; Balenkova , E. S. Efficient syntheses of new CF3-containing diazolopyrimidines . Synthesis 2002 , 1 , 133 – 137 ; (b) Lipson, V. V.; Orlov, V. D.; Desenko, S. M.; Shishkina, S. V.; Shishkin, O. V.; Shirobokova, M. G. 1,2,3,4-Tetrahydropyrimido[1,2-a]benzimidazole-2 and -4-ones, Chem. Het. Compd. 2000, 36(9), 1039–1042; (d) Afeefy, H. Y. Synthesis of new pyrimido[1,2]benzimidazole and triazole[1,5-a]pyrimidine. Boll. Chim. Farm. 1998, 137(11), 480–483; (e) Asobo, P. F.; Wahe, H.; Mabafor, J. T.; Nkengfack, A. E. Fonum, Z. T.; Sopbue, E. F.; Dopp, D. J. The formation of novel biologically active pyrimido[1,2-a]benzimidazoles from allenicnitriles and aminobenzimidazoles. Chem. Soc. Perkin Trans. 2001, 457–461; (f) Wahe, H.; Asobo, P. F.; Cherkasov, R. A.; Fomum, Z. T.; Doepp, D. Formation of pyrimido[1,2-a]benzimidazoles and oxazolo[3,2-a]benzimidazoles. Arkivoc 2004, (1), 130; (g) Dawood, K. M.; Farog, A. M.; Kandeel, Z. E. J. Chem. Res,. Syno. 1999, 88; (h) Al-Afaleq Eljazi, I. Heterocyclic synthesis via naminonitriles. Synth. Commun. 2000, 30(11), 1985–1999 .
   Google Scholar
• (a) Dandia , A. ; Singh , R. ; Khaturia . Efficient microwave enhanced solvent-free synthesis of potent antifungal fluorinated benzothiazepine fused β-lactam derivatives . J. Fluorine Chem. 2007 , 128 , 524 – 529 ; (b) Dandia, A.; Singh, R.; Khaturia, S. Microwave enhanced solid support synthesis of fluorine containing benzopyrano-triazolo-thiadiazepines as potent antifungal agents. Bioorg. Med. Chem. 2006, 14, 1303–1308; (c) Dandia, A.; Arya, K.; Sati, M.; Gautam, S. Microwave assisted green chemical synthesis of novel spiro [indole-pyrido thiazines]: A system reluctant to be formed under thermal conditions. Tetrahedron 2004, 60, 5253–5258; (d) Dandia, A.; Sati, M.; Arya, K.; Loupy, A. Dry-media one-pot syntheses of fluorinated-2,3-dihydro-1,5-benzothiazepines under microwave activation. Green Chem. 2002, 4, 599–602; (e) Dandia, A.; Sachdeva, H.; Singh, R. J. Chem. Res,. Synop. 2000, 272–275 .
   Web of Science ®Google Scholar
• (a) Dandia , A. ; Arya , K. ; Sarawgi , P. Facile one-pot green chemical synthesis of 1,3,5-tri-(quinazolinyl/benzothiazolyl/benzimidazolyl)-s-triazines in aqueous medium under microwaves . J. Indian Chem. Soc. 2003 , 80 , 1183 – 1186 ; (b) Dandia, A.; Arya, K.; Sati, M.; Sarawgi, P. J. Fluorine Chem. 2004, 125, 1273–1277; (c) Dandia, A.; Arya, K.; Sati, M. Microwave assisted synthesis of fluorinated hexahydro-1,3,5-triazine derivatives in aqueous medium and one-pot synthesis of 1,2,4-triazolo-(4,3-a)-1,3,5-triazines. Synth. Commun. 2004, 34(6), 1141–1155 .
   Web of Science ®Google Scholar
• (a) Breslow , R. Hydrophobic effects on simple organic reactions in water. Acc. Chem. Res. 1991, 24, 159; (b) Otto, S.; Engberts J. B. F. N. Diels-Alder reactions in water. Pure Appl. Chem. 2000, 72, 1365–1372; (c) Otto, S.; Engberts, J. B. F. N. Hydrophobic interactions and chemical reactivity. Org. Biomol. Chem. 2003, 1, 2809–2820.
   Web of Science ®Google Scholar