A reexamination of Biginelli-like multicomponent condensation reaction: One-pot regioselective synthesis of spiro heterobicyclic rings

Molecular Diversity

Volumn 8, Issue 2, 2004, Pages 141-145

  Shaabani, Ahmad ^a   Bazgir, Ayoob ^a   Bijanzadeh, Hamid Reza ^b  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Barbituric acid; Biginelli reaction; Meldrum's acid; Multicomponent; Solvent free; Spiro heterobicyclic rings

Indexed keywords

ALDEHYDE; BARBITURIC ACID DERIVATIVE; DIAMIDE; ESTER; HETEROCYCLIC COMPOUND; UREA;

ARTICLE; BIGINELLI REACTION; CATALYST; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

ALDEHYDES; AMIDES; BARBITURATES; BICYCLO COMPOUNDS, HETEROCYCLIC; BIOCHEMISTRY; ESTERS; UREA;

EID: 3543031001     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000025613.35304.25     Document Type: Article

References (24)

1. (a) Domling, A. and Ugi, I., Multicomponent reaction with isocyanides, Angew. Chem. Int. Ed., 39 (2000) 3168-3210.
2. (b) Kappe, C.O., High-speed combinatorial synthesis utilizing microwave irradiation, Curr. Opin. Chem. Biol., 6 (2002) 314-320.
3. (c) Domling, A., Recent advances in isocyanide-based multicomponent chemistry, Curr. Opin. Chem. Biol., 6 (2002) 306-313.
4. Biginelli, P., Gazz. Chim. Ital., 23 (1893) 360.
5. (a) Kappe, C.O., 100 Years of the Biginelli dihydropyrimidine synthesis, Tetrahedron, 49 (1993) 6937-6963, and references therein,
6. (b) Sabitha, G., Reddy, G.S.K.K., Reddy, K.B. and Yadav, J.S, Vanadium(III) chloride catalyzed Biginelli condensation: Solution phase library generation of dihydropyrimidin-2(1H)-ones, Tetrahedron Lett., 44 (2003) 6497-6499.
7. Yarim, M., Sarac, S., Kilic, F.S. and Erol, K., Synthesis and in vitro calcium antagonist activity of 4-aryl-7,7-dimethyl/1,7,7-trimethyl-1,2,3,4,5,6, 7,8-octahydroquinazohne-2,5-dione derivatives, IL Farmaco, 58 (2002) 17-24.
8. Byk, G., Gettlieb, H. E., Herscovici, J. and Mirkin, E, New regioselective multicomponent reaction: One pot synthesis of spiro hetembicyclic aliphatic rings, J. Comb. Chem., 2 (2000) 732-735.
9. (a) Mokrosz, J.L., Paluchowska, M.H., Szneler, E. and Drozdz, B., The effect of aryl substituents in some spiro[2-oxo-4,6-bis(aryl) hexahydropyrimidine-5,5′-barbituric acids], Arch. Pharm. (Weinheim, Germany), 322 (1989) 231-235.
10. (b) Mamaev, V.P. and Borovik, V.P., spiro[2-oxo-4,6- diphenylhexahydropyrimidine-5,5′-barbituric acid], Izobret., Prom. Obraztsy, Tovarnye Znaki, 45 (1968) 24; Chem. Abstr., 69 (1968) 96790.
11. (b) Mamaev, V.P. and Borovik, V.P., spiro[2-oxo-4,6- diphenylhexahydropyrimidine-5,5′-barbituric acid], Izobret., Prom. Obraztsy, Tovarnye Znaki, 45 (1968) 24; Chem. Abstr., 69 (1968) 96790.
12. (c) Mamaev, V.P., Borovik, V.P., Gorfinkel, M.I. and Ivanovskaya, L. Yu., Route for the synthesis of spiropyrimidinebarbituric acids, Izv. Akad. Nauk SSSR, Ser. Khim. (1970) 1637-1638; Chem. Abstr., 74 (1971) 22276.
13. (c) Mamaev, V.P., Borovik, V.P., Gorfinkel, M.I. and Ivanovskaya, L. Yu., Route for the synthesis of spiropyrimidinebarbituric acids, Izv. Akad. Nauk SSSR, Ser. Khim. (1970) 1637-1638; Chem. Abstr., 74 (1971) 22276.
14. (d) Borovik, V.P. and Mamaev, V.P., Synthesis of sulfur-containing spiropyrimidine barbituric acids, Khim. Farm. Zh. 4 (1970) 32-35; Chem. Abstr., 72 (1970) 111411.
15. (d) Borovik, V.P. and Mamaev, V.P., Synthesis of sulfur-containing spiropyrimidine barbituric acids, Khim. Farm. Zh. 4 (1970) 32-35; Chem. Abstr., 72 (1970) 111411.
16. Shaabani, A., Bazgir, A. and Teimouri, F., Ammonium chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions, Tetrahedron Lett., 44 (2003) 857-859.
17. Shaabani, A., Teimouri, M.B. and Bijanzadeh, H.R., One-pot three component condensation reaction in water: An efficient and improved procedure for the synthesis of furo[2,3-d]pyrimidine-2,4(1H,3H)-diones, Tetrahedron Lett., 43 (2002) 9151-9154.
18. Shaabani, A. and Teimouri, M.B., The reaction of alkyl isocyanides and benzylidene Meldrum's acid derivatives in the presence of water: A one-pot synthesis of 4-(alkylamino)-3-aryl-4-oxobutanoic acids, J. Chem. Research(S), (2002) 433-435.
19. Shaabani, A., Yavari, I., Teimouri, M.B., Bazgir, A. and Bijanzadeh, H.R., New and efficient synthesis of dialkyl 2-[1-p-nitrophenyl-2-(alkylamino)- 2-oxoethyl]malonates, Tetrahedron, 57 (2001) 1375-1378.
20. Folkers, K. and Johnson, T.B., Researches on pyrimidines. CXXXVI. The mechanism of formation of tetrahydropyrimidines by the Biginelli reaction, J. Am. Chem. Soc., 55 (1933) 3784-3791.
21. Kappe, C.O., A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-acyliminium ion intermediate, J. Org. Chem., 62 (1997) 7201-7204.
22. Sweet, F. and Fissekis, J.D., On the synthesis of 3,4-dihydropyrimidin-2- (1H)-ones and the mechanism of the Biginelli reaction, J. Am. Chem. Soc., 95 (1973) 8741-8749.
23. Bigi, F., Carloni, S., Ferrari, L., Maggi, R., Mazzacani, A. and Sartori, G., Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes, Tetrahedron Lett., 42 (2002) 5203-5205.
24. Kaup, G., Reza Naim Jamal, M. and Schmeyers, J., Solvent-free Knoevenagel condensation and Michael additions in the solid state and in the melt with quantitative yield, Tetrahedron, 59 (2003) 3753-3760.