Molecular Diversity from the L-Proline-Catalyzed, Three-Component Reactions of 4-Hydroxycoumarin, Aldehyde, and 3-Aminopyrazole or 1,3-Dimethyl-6-aminouracil

REFERENCES

• Zhu, J.; Bienayme, H. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005.
   Google Scholar
• Tejedor, D.; Garcia-Tellado, F. Chemo-differentiating ABB’ multicomponent reactions: Privileged building blocks. Chem. Soc. Rev. 2007, 36, 484–491.
   PubMed Web of Science ®Google Scholar
• Cadierno, V.; Gimeno, J.; Nebra, N. A novel propargylation/cycloisomerization tandem process catalyzed by a ruthenium(II)/trifluoroacetic acid system: One-pot entry to fully substituted furans from readily available secondary propargylic alcohols and 1,3-dicarbonyl compounds. Adv. Synth. Catal. 2007, 349, 382–394.
   Web of Science ®Google Scholar
• Yu, D.; Suzuki, M.; Xie, L.; Morris-Natschke, S. L.; Lee, K. H. Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med. Res. Rev. 2003, 23, 322–345.
   PubMed Web of Science ®Google Scholar
• Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis, and biological activity. Curr. Med. Chem. 2005, 12, 887–916.
   PubMed Web of Science ®Google Scholar
• Tangmouo, J. G.; Meli, A. L.; Komguem, J.; Kuete, V.; Ngounou, F. N.; Lontsi, D.; Beng, V. P.; Choudhary, M. I.; Sondengam, B. L. Crassiflorone, a new naphthoquinone from Diospyroscrassiflora (Hien). Tetrahedron Lett. 2006, 47, 3067–3070.
   Web of Science ®Google Scholar
• Kraus, G. A.; Kim, I. A direct synthesis of o-methylclaussequinone. J. Org. Chem. 2003, 68, 4517–4518.
   PubMed Web of Science ®Google Scholar
• Siddiqui, I. R.; Shamin, S.; Singh, A.; Srivastava, V.; Yadav, S. Moisture compatible and recyclable indium(III) chloride–catalyzed and microwave-assisted efficient route to substituted 1H-quinolin-2-ones. Arkivoc 2010, 11, 232–241.
   Web of Science ®Google Scholar
• Satynarayana, V. S. V.; Sreevani, P.; Sivakumar, A.; Vijayakumar, V. Synthesis and antimicrobial activity of new Schiff bases containing coumarin moiety and their spectral characterization. Arkivoc 2008, 17, 221–233.
   Google Scholar
• Desai, J. T.; Desai, C. K.; Desai, K. R. A convenient, rapid, and ecofriendly synthesis of isoxazoline heterocyclic moiety containing bridge at 2°-amine as potential pharmacological agent. J. Iran. Chem. Soc. 2008, 5, 67–73.
   Web of Science ®Google Scholar
• Schreiber, S. L. Target-oriented and diversity-oriented organic synthesis in drug discovery. Science 2000, 287, 1964–1969.
   PubMed Web of Science ®Google Scholar
• Dömling, A. Recent advances in isocyanide-based multicomponent chemistry. Curr. Opin. Chem. Biol. 2002, 6, 306–313.
   PubMed Web of Science ®Google Scholar
• Murray, R. D. H.; Mendez, J.; Brown, S. A. The Nature of Coumarin: Chemistry and Biochemistry; Wiley: New York, 1982.
   Google Scholar
• (a) Valentin, A.; Chebanov, Katerina, A.; Gura, Sergey, M. Aminopyrazoles as key reagents in multicomponent heterocyclizations. Desenko Top. Heterocycl. Chem. 2010, 23, 41–84; (b) Dias, L. R. S.; Santos, M. B.; de Albuquerque, S.; Castro, H. C.; de Souza, A. M. T.; Freitas, A. C. C.; DiVaio, M. A. V.; Cabral, L. M.; Rodrigues, C. R. Synthesis, in vitro evaluation, and SAR studies of a potential antichagasic 1H-pyrazolo[3,4-b]pyridine series. Bioorg. Med. Chem. 2007, 15, 211–219.
   Google Scholar
• (a) Lunt, E.; Newton, C. C. In Comprehensive Heterocyclic Chemistry; A. R. Katritzky, C. W. Rees, A. J. Boulton, A. McKillop (Eds.); Pergamon: Oxford, 1984; vol. 3, pp. 199, 232, 260–261; (b) Bradskaw, T. K.; Hutchinson, D. W. 5-Substituted pyrimidine nucleosides and nucleotides. Chem. Soc. Rev. 1977, 6, 43–62.
   Google Scholar
• Pal, S.; Khan, M. N.; Karamthulla, S.; Choudhury, L. H. Molecular iodine–catalyzed one-pot multicomponent reactions for the synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones. RSC Adv. 2013, 3, 15705–15711.
   Web of Science ®Google Scholar
• Ghosh, A.; Khan, A. T. Synthesis of dihydrochromeno[4,3-b]pyrazolo[4,3-e]pyridin-6(7H)-ones involving one-pot three-component tandem Knoevenagel–Michael reaction catalyzed by n-tetrabutylammonium tribromide (TBATB). Tetrahedron Lett. 2014, 55, 2006–2009.
   Web of Science ®Google Scholar
• David, W. C. The advent and development of organocatalysis. Nature 2008, 455, 304–308.
   PubMed Web of Science ®Google Scholar
• Panday, S. K. Advances in the chemistry of proline and its derivatives: An excellent amino acid with versatile applications in asymmetric synthesis. Tetrahedron: Asymmetry 2011, 22, 1817–1847.
   Web of Science ®Google Scholar
• Karamthulla, S.; Pal, S.; Parvin, T.; Choudhury, L. H. L-Proline-catalyzed multicomponent reactions: Facile access to 2H-benzo[g]pyrazolo[3,4-b]quinoline-5,10(4H,11H)-dione derivatives. RSC Adv. 2014, 4, 15319–15324.
   Web of Science ®Google Scholar
• Bharti, R.; Parvin, T. One-pot synthesis of highly functionalized tetrahydropyridines: A camphoresulfonic acid–catalyzed multicomponent reaction. J. Heterocycl. Chem. In press. doi: 10.1002/jhet.2268.
   Web of Science ®Google Scholar