Divergent Synthesis of novel five-membered heterocyclic compounds by base-mediated rearrangement of acrylamides derived from a novel isocyanide-based multicomponent reaction

Molecules

Volumn 16, Issue 10, 2011, Pages 8775-8787

  Basso, Andrea ^a   Banfi, Luca ^a   Riva, Renata ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

Diversity Oriented Synthesis; Isocyanides; Multicomponent reactions; Rearrangement reactions

Indexed keywords

EID: 80054930200     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16108775     Document Type: Article

References (12)

1. Zhu, J. P. Recent developments in the isonitrile-based multicomponent synthesis of heterocycles. Eur. J. Org. Chem. 2003, 1133-1144.
2. Orru, R. V. A.; Ruijter, E. Synthesis of Heterocycles via Multicomponent Reactions; Springer-Verlag: Berlin/Heidelberg, Germany, 2010; pp. 1-277.
3. Basso, A.; Banfi, L.; Galatini, A.; Guanti, G.; Rastrelli, F.; Riva, R. Isocyanides and arylacetic acids: Synthesis and reactivity of 3-aryl-2-acyloxyacrylamides, an example of serendipity-oriented synthesis. Org. Lett. 2009, 11, 4068-4071.
4. Ugi, I.; Rosendhal, K.; Isonitrile, V. I. Umsetzungen von Isonitrilen mit Ketenen. Chem. Ber. 1961, 94, 2233-2235.
5. Mossetti, R.; Pirali, T.; Tron, G. C.; Zhu, J. P. Efficient synthesis of alpha-ketoamides via 2-acyl-5-aminooxazoles by reacting acyl chlorides and alpha-isocyanoacetamides. Org. Lett. 2010, 12, 820-823.
6. Li, X.; Danishefsky, S. J. New chemistry with old-functional groups: On the reaction of isonitriles with carboxylic acids-A route to various amide types. J. Am. Chem. Soc. 2008, 130, 5446-5448. (Pubitemid 351612951)
7. Nef, J. U. Ueber das zweiwerthige Kohlenstoffatom. Justus Liebigs Ann. Chem. 1892, 270, 267-335.
8. Bernier, D.; Moser, F.; Brückner, R. Synthesis and cyclization of 3-aryl-2-(arylacetoxy) acrylates: A three-step access to pulvinones. Synthesis 2007, 2240-2248. (Pubitemid 47242662)
9. Basso, A.; Banfi, L.; Riva, R. A marriage of convenience: Combining the power of isocyanidebased multicomponent reactions with the versatility of (hetero) norbornene chemistry. Eur. J. Org. Chem. 2010, 1831-1841.
10. Pendri, A.; Troyer, T. L.; Sofia, M. J.; Walker, M. A.; Naidu, B. N.; Benville, J.; Meanwell, N. A.; Dicker, I.; Lin, Z.; Krystal, M.; Gerritz, S. W. Solid phase synthesis of novel pyrrolidinedione analogs as potent HIV-1 integrase inhibitors. J. Comb. Chem. 2010, 12, 84-90.
11. Moon, J. T.; Jeon, J. Y.; Park, H. A.; Noh, Y.-S.; Lee, K.-T.; Kim, J.; Choo, D. J.; Lee, J. Y. Synthesis and PGE2 production inhibition of 1H-furan-2, 5-dione and 1H-pyrrole-2, 5-dione derivatives. Bioorg. Med. Chem. Lett. 2010, 20, 734-737.
12. Open Innovation Drug Discovery Home Page. Available online: https://openinnovation. lilly.com/dd/about-open-innovation/what-are-pd2-and- targetd2.html (accessed on 13 October 2011).