One-Pot Annulation of Pyrimidine Ring on Azoles Under Microwave Irradiation and Solvent-Free Conditions

Abstract

Azole Schiff bases 2a-f are annulated diastereoselectively with glycine and acetic anhydride, under microwave irradiation and solvent-free conditions, to yield 6,7-dihydro-5H-1,3,4-oxa(thia)diazolo[3,2-a]pyrimidin-5-ones 4a-f in a one-pot procedure.

Key words

Schiff bases - 1,3,4-oxa(thia)diazolopyrimidines - solvent free - microwave - stereoselective synthesis

References

• 1 Whitley RJ. Alford C. Ann. Rev. Microbiol.  1978,  32:  285 
• 2 Nielsen FE. Pedersen EB. Tetrahedron  1982,  38:  1435 
• 3 inventors; Jpn. Kokai Tokkyo Koho JP  5962595 (to S. S. Pharma-ceutical Co. Ltd.).  ; Chem. Abstr. 1984, 101, 72754
• 4 Yadav LDS. Saigal S. Indian J. Chem.  1995,  34B:  500 
• 5 Pees KJ, and Albert G. inventors; US Patent  5 593 996.  ; Chem. Abstr. 1997, 126, 171605
• 6 Pfrengle W, and Franz A. inventors; Jpn. Kokai Tokkyo Koho JP  1135581.  ; Chem. Abstr. 1999, 130, 168390
• 7a Caddick S. Tetrahedron  1995,  51:  10403 
• 7b Loupy A. Petit A. Hamelin J. Texier-Boullet F. Jacquault P. Mathe D. Synthesis  1998,  1213 
• 7c Lidstrom P. Tierney J. Wathey B. Westman J. Tetrahedron  2001,  57:  9225 
• 7d Varma RS. Green Chem.  1999,  1:  43 
• 8 Perreux L. Loupy A. Tetrahedron  2001,  57:  9199 
• 9 Yadav LDS. Kapoor R. Synthesis  2002,  1502 
• 10 Yadav LDS. Sharma S. Synthesis  1993,  864 
• 11 Yadav LDS. Saigal S. Pal DR. J. Chem. Res., Synop.  1998,  307 
• 12 Raner KD. Strauss CR. Vyskoc F. Mokbel L. J. Org. Chem.  1993,  58:  950 
• 13 Booth SE. Jenkins PR. Swain CJ. J. Chem. Soc., Chem. Commun.  1991,  1248 
• 14 Hirayama M. Gamoh K. Ikekawa N. Chem. Lett.  1982,  491 
• 15 Mukaiyama T. Iwasawa N. Chem. Lett.  1984,  753 
• 16 Tanikaga R. Hamamura K. Kaji A. Chem. Lett.  1988,  977