메뉴 건너뛰기




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

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

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;

EID: 3543031001     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000025613.35304.25     Document Type: Article
Times cited : (47)

References (24)
  • 1
    • 2542509173 scopus 로고    scopus 로고
    • Multicomponent reaction with isocyanides
    • (a) Domling, A. and Ugi, I., Multicomponent reaction with isocyanides, Angew. Chem. Int. Ed., 39 (2000) 3168-3210.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3168-3210
    • Domling, A.1    Ugi, I.2
  • 2
    • 0036603599 scopus 로고    scopus 로고
    • High-speed combinatorial synthesis utilizing microwave irradiation
    • (b) Kappe, C.O., High-speed combinatorial synthesis utilizing microwave irradiation, Curr. Opin. Chem. Biol., 6 (2002) 314-320.
    • (2002) Curr. Opin. Chem. Biol. , vol.6 , pp. 314-320
    • Kappe, C.O.1
  • 3
    • 0036603766 scopus 로고    scopus 로고
    • Recent advances in isocyanide-based multicomponent chemistry
    • (c) Domling, A., Recent advances in isocyanide-based multicomponent chemistry, Curr. Opin. Chem. Biol., 6 (2002) 306-313.
    • (2002) Curr. Opin. Chem. Biol. , vol.6 , pp. 306-313
    • Domling, A.1
  • 5
    • 0027205552 scopus 로고
    • 100 Years of the Biginelli dihydropyrimidine synthesis
    • and references therein
    • (a) Kappe, C.O., 100 Years of the Biginelli dihydropyrimidine synthesis, Tetrahedron, 49 (1993) 6937-6963, and references therein,
    • (1993) Tetrahedron , vol.49 , pp. 6937-6963
    • Kappe, C.O.1
  • 6
    • 0043199389 scopus 로고    scopus 로고
    • Vanadium(III) chloride catalyzed Biginelli condensation: Solution phase library generation of dihydropyrimidin-2(1H)-ones
    • (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.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6497-6499
    • Sabitha, G.1    Reddy, G.S.K.K.2    Reddy, K.B.3    Yadav, J.S.4
  • 7
    • 0041967088 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2002) IL Farmaco , vol.58 , pp. 17-24
    • Yarim, M.1    Sarac, S.2    Kilic, F.S.3    Erol, K.4
  • 8
    • 0037660637 scopus 로고    scopus 로고
    • New regioselective multicomponent reaction: One pot synthesis of spiro hetembicyclic aliphatic rings
    • 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.
    • (2000) J. Comb. Chem. , vol.2 , pp. 732-735
    • Byk, G.1    Gettlieb, H.E.2    Herscovici, J.3    Mirkin, E.4
  • 9
    • 0024560217 scopus 로고
    • The effect of aryl substituents in some spiro[2-oxo-4,6-bis(aryl) hexahydropyrimidine-5,5′-barbituric acids]
    • Weinheim, Germany
    • (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.
    • (1989) Arch. Pharm. , vol.322 , pp. 231-235
    • Mokrosz, J.L.1    Paluchowska, M.H.2    Szneler, E.3    Drozdz, B.4
  • 10
    • 1542287118 scopus 로고
    • Spiro[2-oxo-4,6-diphenylhexahydropyrimidine-5,5′-barbituric acid], Izobret
    • (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.
    • (1968) Prom. Obraztsy, Tovarnye Znaki , vol.45 , pp. 24
    • Mamaev, V.P.1    Borovik, V.P.2
  • 11
    • 26144432139 scopus 로고
    • (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.
    • (1968) Chem. Abstr. , vol.69 , pp. 96790
  • 13
    • 26144458538 scopus 로고
    • (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.
    • (1971) Chem. Abstr. , vol.74 , pp. 22276
  • 14
    • 1542287117 scopus 로고
    • Synthesis of sulfur-containing spiropyrimidine barbituric acids
    • (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.
    • (1970) Khim. Farm. Zh. , vol.4 , pp. 32-35
    • Borovik, V.P.1    Mamaev, V.P.2
  • 15
    • 26144443562 scopus 로고
    • (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.
    • (1970) Chem. Abstr. , vol.72 , pp. 111411
  • 16
    • 0037455089 scopus 로고    scopus 로고
    • Ammonium chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2- (1H)-ones under solvent-free conditions
    • 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.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 857-859
    • Shaabani, A.1    Bazgir, A.2    Teimouri, F.3
  • 17
    • 0037049217 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 9151-9154
    • Shaabani, A.1    Teimouri, M.B.2    Bijanzadeh, H.R.3
  • 18
    • 0036760083 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2002) J. Chem. Research(S) , pp. 433-435
    • Shaabani, A.1    Teimouri, M.B.2
  • 19
    • 0035843379 scopus 로고    scopus 로고
    • New and efficient synthesis of dialkyl 2-[1-p-nitrophenyl-2-(alkylamino)- 2-oxoethyl]malonates
    • 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.
    • (2001) Tetrahedron , vol.57 , pp. 1375-1378
    • Shaabani, A.1    Yavari, I.2    Teimouri, M.B.3    Bazgir, A.4    Bijanzadeh, H.R.5
  • 20
    • 0004857277 scopus 로고
    • Researches on pyrimidines. CXXXVI. The mechanism of formation of tetrahydropyrimidines by the Biginelli reaction
    • 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.
    • (1933) J. Am. Chem. Soc. , vol.55 , pp. 3784-3791
    • Folkers, K.1    Johnson, T.B.2
  • 21
    • 0030732273 scopus 로고    scopus 로고
    • A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-acyliminium ion intermediate
    • 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.
    • (1997) J. Org. Chem. , vol.62 , pp. 7201-7204
    • Kappe, C.O.1
  • 22
    • 33947086781 scopus 로고
    • On the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and the mechanism of the Biginelli reaction
    • 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.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 8741-8749
    • Sweet, F.1    Fissekis, J.D.2
  • 23
    • 0035974365 scopus 로고    scopus 로고
    • Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes
    • 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.
    • (2002) Tetrahedron Lett. , vol.42 , pp. 5203-5205
    • Bigi, F.1    Carloni, S.2    Ferrari, L.3    Maggi, R.4    Mazzacani, A.5    Sartori, G.6
  • 24
    • 0038737165 scopus 로고    scopus 로고
    • Solvent-free Knoevenagel condensation and Michael additions in the solid state and in the melt with quantitative yield
    • 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.
    • (2003) Tetrahedron , vol.59 , pp. 3753-3760
    • Kaup, G.1    Reza Naim Jamal, M.2    Schmeyers, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.