Synthesis of Coumarines and 4H-Chromenes through the Reaction of tert-Butyl Isocyanide and Dialkyl Acetylenedicarboxylates in Presence of 2-Hydroxybenzaldehydes

Abstract

An effective route to novel coumarines and 4H-chromenes is described. This involves the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-hydroxybenzaldehydes.

Key words

4H-chromenes - coumarines - alkyl isocyanides - 2-hydroxybenzaldehyde

References

• 1 Ellis GP. Chromenes, Chromanones and Chromones   Wiley; New York: 1971. 
• 2 Murray DH. Mendes J. Brown SA. The Nature of Coumarins: Occurance, Chemistry and Biochemistry   Wiley; New York: 1982. 
• 3 Cruz-Almanza R. Perez-Flores F. Lemini C. Heterocycles  1994,  37:  795 
• 4 Cassidy F. Evans JM. Hadley MS. Haladiy AH. Leach PE. Stemp G. J. Med. Chem.  1992,  35:  1623 
• 5 Van TN. Debenedetti S. De Kimpe N. Tetrahedron Lett.  2003,  44:  4199 
• 6 Parker KA. Mindt TL. Org. Lett.  2001,  3:  3875 
• 7 Kumar P. Bodas MS. Org. Lett.  2000,  2:  3821 
• 8 Melini L. Adv. Heterocycl. Chem.  1975,  18:  159 
• 9 Hepworth JD. In Comprehensive Heterocyclic Chemistry   Vol. 3:  Katritzky AR. Rees CW. Pergamon; Oxford: 1984.  p.573-883  
• 10 Davis SG. Mobbs BE. Goodwin CJ. J. Chem. Soc., Perkin Trans. 1  1987,  2597 
• 11 Yavari I. Adib M. Hojabri L. Tetrahedron  2001,  57:  7537 
• 12 Yavari I. Anary-Abbasinejad M. Alizadeh A. Hossaini Z. Tetrahedron  2003,  59:  1289 
• 13 Ugi I. Isonitrile Chemistry   Academic Press; London: 1971. 
• 14 Ugi I. Angew. Chem., Int. Ed. Engl.  1982,  21:  810 
• 15 Domling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
• 16 Walborsky HM. Periasamy MP. In The Chemistry of Functional Groups, Supplement C   Patai S. Rappoport Z. Wiley; New York: 1983.  Chap. 20. p.835 
• 17 Marcaccini S. Torroba T. Org. Prep. Proced. Int.  1993,  25:  141