Facile, One-Pot Synthesis of Bicyclic 2-Pyridones from Acyl Isocyanates, N-Phenylmaleimide and Trimethylsilyldiazomethane

Abstract

The hetero-Diels-Alder reaction of 2-substituted 4-tri­methylsiloxyoxazoles, prepared in situ from trimethylsilyldiazo­methane and acyl isocyanates, with N-phenylmaleimide followed by treatment with a catalytic amount of 10-camphorsulfonic acid efficiently gave bicyclic 2-pyridones in a one-pot process.

Key words

acyl isocyanates - Diels-Alder reaction - 2-pyridones - oxazoles - trimethylsilyldiazomethane

References

• 1 Kondra’eva GYa. Khim. Nauka Prom.  1957,  2:  666 ; Chem. Abstr.; 1958, 52, 6345
• For reviews:
• 2a Turchi IJ. Dewar MJS. Chem. Rev.  1975,  75:  389 
• 2b Boger DL. Tetrahedron  1983,  39:  2869 
• 2c Boger DL. Chem. Rev.  1986,  86:  781 
• 2d Levin JI. Laakso LM. Heterocyclic Compounds   Vol. 60:  Palmer DC. Wiley; New York: 2003.  p.417 
• Recent reports:
• 3a Lopez FJ. Jett M.-F. Muchowski JM. Nitzan D. O’Yang C. Heterocycles  2002,  56:  91 
• 3b Efremov I. Paquette LA. Heterocycles  2002,  56:  35 
• 3c Janvier P. Sun X. Bienaymé H. Zhu J. J. Am. Chem. Soc.  2002,  124:  2560 
• 3d Janvier P. Bienaymé H. Zhu J. Angew. Chem. Int. Ed.  2002,  41:  4291 
• 3e Dumond YR. Gum AG. Molecules  2003,  8:  873 
• 3f Ohba M. Natsutani I. Sakuma T. Tetrahedron Lett.  2004,  45:  6471 
• 3g Ohba M. Natsutani I. Heterocycles  2004,  63:  2845 
• 3h Sandford G. Wilson I. Timperley CM. J. Fluorine Chem.  2004,  125:  1425 
• 3i Bondock S. Heteroat. Chem.  2005,  16:  49 
• 4 Potts KT. Marshall JL. J. Org. Chem.  1979,  44:  626 
• 5 Hari Y. Iguchi T. Aoyama T. Synthesis  2004,  1359 
• 6a Matsuo T. Miki T. Chem. Pharm. Bull.  1972,  20:  669 
• 6b Shimada S. J. Heterocycl. Chem.  1987,  24:  1237