N-Bromosuccinimide as an Almost Neutral Catalyst for Efficient Synthesis of Dihydropyrimidinones Under Microwave Irradiation

Abstract

NBS has been used as a mild, efficient and almost neutral catalyst for the preparation of dihydropyrimidinones (DHPMs) and the corresponding thio-derivatives under microwave irradiation. By this method, a wide variety of DHPMs were synthesized in good to high yields.

Key words

N-bromosuccinimide - dihydropyrimidinones - microwave irradiation

References

• 1a Cho H. Ueda M. Shima K. Mizuno A. Hayashimatsu M. Ohnaka Y. Takeuchi Y. Hamaguchi M. Aisaka K. Hidaka T. Kawai M. Takeda M. Ishihara T. Funahashi K. Satah F. Morita M. Noguchi T. J. Med. Chem.  1989,  32:  2399 
• 1b Atwal KS. Rovnyak GC. Kimball SD. Floyd DM. Moreland S. Swanson BN. Gougoutas JZ. Schwartz J. Smillie KM. Malley MF. J. Med. Chem.  1990,  33:  2629 
• 1c Rovnyak GC. Kimball SD. Beyer B. Cucinotta G. Dimarco JD. Gougoutas J. Hedberg AÓ. Malley M. McCarthy JP. Zhang R. Moreland S. J. Med. Chem.  1995,  38:  119 
• 2a Atwal KS. Swanson BN. Unger SE. Floyd DM. Moreland S. Hedberg AÓ. Reilly BC. J. Med. Chem.  1991,  34:  806 
• 2b Grover GJ. Dzwonczyk S. McMullen DM. Normadinam CS. Sleph PG. Moreland SJ. J. Cardiovasc. Pharmacol.  1995,  26:  289 
• 3 Snider BB. Shi Z. J. Org. Chem.  1993,  58:  3823 
• 4a Patil AD. Kumar NV. Kokke WC. Bean MF. Freyer AJ. De Brosse C. Mai S. Truneh A. Faulkner DJ. Carte B. Breen AL. Hertzberg RP. Johnson RK. Westly JW. Potts BCM. J. Org. Chem.  1995,  60:  1182 
• 4b Rama Rao AV. Gujar MK. Vasudevan J. J. Chem. Soc., Chem. Commun.  1995,  1369 
• 4c Snider BB. Chen J. Patil AD. Freyer A. Tetrahedron Lett.  1996,  37:  6977 
• 5a Biginelli P. Gazz. Chem. Ital.  1893,  23:  360 
• 5b For a review see also: Kappe CO. Tetrahedron  1993,  49:  6937 
• 6 Fu NY. Yuan YF. Cao Z. Wang SW. Wang JT. Peppe C. Tetrahedron  2002,  58:  4801 
• 7 Ranu B. Hajra A. Jana U. J. Org. Chem.  2000,  65:  6270 
• 8 Yadav JS. Reddy BVS. Srinivas R. Venugopal C. Ramalingam T. Synthesis  2001,  1341 
• 9a Lu J. Ma H. Synlett  2000,  63 
• 9b Lu J. Bai Y. Synthesis  2002,  466 
• 10 Jin T. Zhang S. Li T. Synth. Commun.  2002,  32:  1847 
• 11 Lu J. Bai Y. Wang Z. Yang B. Ma H. Tetrahedron Lett.  2000,  41:  9075 
• 12 Varala R. Alam MM. Adapa SR. Synlett  2003,  67 
• 13 Hu EH. Slider DR. Dolling U.-H. J. Org. Chem.  1998,  63:  3454 
• 14 Kappe CO. Kumar D. Varma RS. Synthesis  1999,  1799 
• 15 Hudlicky M. Oxidations in Organic Chemistry   ACS Monograph 186; American Chemical Society; Washington, DC: 1990. 
• 16 Karimi B. Ebrahimian GR. Seradj H. Org. Lett.  1999,  1:  1737 
• 17 Karimi B. Seradj H. Ebrahimian GR. Synlett  2000,  623 
• 18 Karimi B. Seradj H. Tabaei MH. Synlett  2000,  1798 
• 19 Karimi B. Seradj H. Maleki J. Tetrahedron  2002,  58:  4513 
• 20a Bandgar BP. Uppalla LS. Sadavarte VS. Synlett  2001,  11 
• 20b Kamal A. Chouhan G. Synlett  2002,  474 
• 20c Kamal A. Chouhan G. Ahmed K. Tetrahedron Lett.  2002,  43:  6947