Facile One-Pot Synthesis of Di- and Tri-Substituted Furans From Acyl Isocyanates Using Trimethylsilyldiazomethane

Abstract

The Diels-Alder reaction of 2-substituted 4-(trimethyl­silyloxy)oxazoles, which were prepared in situ from trimethylsilyldiazomethane and acyl isocyanates, with dimethyl acetylenedicarboxylate or ethyl propiolate gave furan-3,4-dicarboxylic or furan-3-carboxylic esters in good yields.

Key words

acyl isocyanates - Diels-Alder reaction - furans - oxazoles - trimethylsilyldiazomethane

References

• 1 Smith AB. Minbiole KP. Freeze S. Synlett  2001,  1739 ; and references cited therein
• 2a Potts KT. Marshall JL. J. Org. Chem.  1979,  44:  626 
• 2b Potts KT. Marshall JL. J. Chem. Soc., Chem., Commun.  1972,  1000 
• 3 Sheehan JC. Izzo PT. J. Am. Chem. Soc.  1949,  71:  4059 
• 4a Langille NF. Dakin LA. Panek JS. Org. Lett.  2002,  4:  2485 
• 4b Schaus JV. Panek JS. Org. Lett.  2000,  2:  469 
• 4c Kelly TR. Lang F. J. Org. Chem.  1996,  61:  4623 
• 4d Balaban AT. Bota A. Dorofeenko GN. Karpenko VD. Ryabukhin YI. Tetrahedron  1978,  34:  2035 
• 4e Rodehorst RM. Koch TH. J. Am. Chem. Soc.  1975,  97:  7298 
• 4f von Troxler F. Helv. Chim. Acta  1973,  56:  1815 
• 4g Rao YS. Filler R. Chem. Commun.  1970,  1622 
• 4h Bird CW. J. Org. Chem.  1962,  27:  4091 
• 5 Moore AJ. Reed DE. Org. Synth. Coll. Vol. V   Wiley; New York: 1954.  p.352 
• Reviews:
• 6a Shioiri T. Aoyama T. Science of Synthesis   Vol. 4:  Fleming I. Georg Thieme Verlag; Stuttgart: 2002.  p.569 
• 6b Shioiri T. Aoyama T. J. Synth. Org. Chem., Jpn.  1996,  54:  918 
• 6c Shioiri T. Aoyama T. Advances in the Use of Synthons in Organic Chemistry   Vol. 1:  Dondoni A. JAI Press Ltd.; London: 1993.  p.51 
• Recent reports:
• 7a Shoji Y. Hari Y. Aoyama T. Tetrahedron Lett.  2004,  45:  1769 
• 7b Hari Y. Tanaka S. Takuma Y. Aoyama T. Synlett  2003,  2151 
• 7c Miyabe R. Shioiri T. Aoyama T. Heterocycles  2002,  57:  1313 
• 8 Boger DL. Weinreb SM. Hetero Diels-Alder Methodology in Organic Synthesis   Wasserman HH. Academic Press, Inc.; San Diego: 1987.  Chap. 10. p.300 
• 9 Novák JJK. Coll. Czech. Chem. Commun.  1975,  40:  2855 
• 10 Chan WH. Lee AWM. Chan ETT. J. Chem. Soc., Perkin Trans. 1  1992,  945 
• 11 Anand RC. Singh V. Heterocycles  1993,  36:  133