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Volumn 34, Issue 18, 2004, Pages 3335-3341

Microwave-assisted efficient synthesis of dihydropyrimidines in solvent-free condition

Author keywords

Biginelli compounds; Ferric chloride hexahydrate; Microwave irradiation; Solvent free condition

Indexed keywords

ALDEHYDE; DIHYDROPYRIDINE DERIVATIVE; ESTER DERIVATIVE; THIOUREA; UREA DERIVATIVE;

EID: 5444266960     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200030577     Document Type: Article
Times cited : (48)

References (31)
  • 1
    • 0000176059 scopus 로고
    • The condensation reaction described by Biginelli
    • Biginelli, P. The condensation reaction described by Biginelli. Gazz. Chim. Ital. 1893, 23, 360.
    • (1893) Gazz. Chim. Ital. , vol.23 , pp. 360
    • Biginelli, P.1
  • 2
    • 5444272402 scopus 로고    scopus 로고
    • 5-Acetyl-3,4,5,6-tertrahydro-4-oxo-2,6-methano-2H-1,3,5, -benzothiazocine(-benzodiazocine)-11-carboxylates. Useful as calcium channel blockers. US Patent 4,609,494, September 2, 1986, Merck and Co., Inc.
    • (a) Baldwin, J.J.; Claremon, D.A.; McClure, D.E. 5-Acetyl-3,4,5,6- tertrahydro-4-oxo-2,6-methano-2H-1,3,5,-benzothiazocine(-benzodiazocine) -11-carboxylates. Useful as calcium channel blockers. US Patent 4,609,494, September 2, 1986, Merck and Co., Inc.;
    • Baldwin, J.J.1    Claremon, D.A.2    McClure, D.E.3
  • 3
    • 5444268075 scopus 로고    scopus 로고
    • Substituted Pyrimidines Useful as Calcium Channel Blockers. US Patent 4,675,321, Jun 23, 1987, Merck and Co., Inc.
    • (b) Baldwin, J.J.; Ptizenberger, S.M.; McClure, D.E.. Substituted Pyrimidines Useful as Calcium Channel Blockers. US Patent 4,675,321, Jun 23, 1987, Merck and Co., Inc.;
    • Baldwin, J.J.1    Ptizenberger, S.M.2    McClure, D.E.3
  • 4
    • 5444251698 scopus 로고    scopus 로고
    • 1,2,3,4-Tetrahydro-6-substituted-4-aryl-3-substituted-2-thioxo(or oxo)-5-pyrimidinecarboxylic acids and esters and use thereof to lower blood pressure. US Patent 4,684,655, 1987, E.R. Squibb and Sons
    • (c) Atwal, K.S. 1,2,3,4-Tetrahydro-6-substituted-4-aryl-3-substituted-2- thioxo(or oxo)-5-pyrimidinecarboxylic acids and esters and use thereof to lower blood pressure. US Patent 4,684,655, 1987, E.R. Squibb and Sons.;
    • Atwal, K.S.1
  • 9
    • 33751385241 scopus 로고
    • Biomimetic synthesis of (±)-crambines A, B, C1 and C2. Revision of the structures of crambines B and C1
    • and references cited therein
    • Sinder, B.B.; Shi, Z. Biomimetic synthesis of (±)-crambines A, B, C1 and C2. Revision of the structures of crambines B and C1. J. Org. Chem. 1993, 58, 3828-3839 and references cited therein.
    • (1993) J. Org. Chem. , vol.58 , pp. 3828-3839
    • Sinder, B.B.1    Shi, Z.2
  • 11
    • 0029069618 scopus 로고
    • An enantiospecific synthesis of the tricyclic guanidine segment of the anti-HIV marine alkaloid batzelladine A
    • (b) Rama Rao, A.V.; Gujar, M.K.; Vasudevan, J. An enantiospecific synthesis of the tricyclic guanidine segment of the anti-HIV marine alkaloid batzelladine A. J. Chem. Soc. Chem. Commun. 1995, 1369-1370;
    • (1995) J. Chem. Soc. Chem. Commun. , pp. 1369-1370
    • Rama Rao, A.V.1    Gujar, M.K.2    Vasudevan, J.3
  • 12
    • 0030599231 scopus 로고    scopus 로고
    • Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D
    • (c) Sinder, B.B.; Patil, A.D.; Freyer, A. Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D Tetrahedron Lett. 1996, 37, 6977-6987.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6977-6987
    • Sinder, B.B.1    Patil, A.D.2    Freyer, A.3
  • 13
    • 33947344341 scopus 로고
    • Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines
    • (a) Folkers, K.; Harwood, H.J.; Johnson, T.B. Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines. J. Am. Chem. Soc. 1932, 54, 3751;
    • (1932) J. Am. Chem. Soc. , vol.54 , pp. 3751
    • Folkers, K.1    Harwood, H.J.2    Johnson, T.B.3
  • 14
    • 0007701406 scopus 로고
    • Wiley: New York, Chapter. 12
    • (b) Brown, D.J. The Pyrimidines; Wiley: New York, 1962; Chapter. 12, 440.
    • (1962) The Pyrimidines , pp. 440
    • Brown, D.J.1
  • 15
    • 0034518876 scopus 로고    scopus 로고
    • Highly versatile solid phase synthesis of bio functional 4-aryl-3,4-dihydropyrimidines using resin-bound isothiourea building blocks and multidirectional resin cleavage
    • Kappe, C.O. Highly versatile solid phase synthesis of bio functional 4-aryl-3,4-dihydropyrimidines using resin-bound isothiourea building blocks and multidirectional resin cleavage. Acc. Chem. Res. 2000, 33, 879-888.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 879-888
    • Kappe, C.O.1
  • 16
    • 0024818583 scopus 로고
    • Synthesis of selectivity functionalized 2-hetero-1,4-dihydropyrimidines
    • (a) Atwal, K.S.; Rovnyak, G.C.; O'Reilly, B.C.; Schrartz, J.J. Synthesis of selectivity functionalized 2-hetero-1,4-dihydropyrimidines. J. Org. Chem. 1989, 54, 5898-5907;
    • (1989) J. Org. Chem. , vol.54 , pp. 5898-5907
    • Atwal, K.S.1    Rovnyak, G.C.2    O'Reilly, B.C.3    Schrartz, J.J.4
  • 17
    • 0031584880 scopus 로고    scopus 로고
    • Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparision of ab initio semiempirical and x-ray crystallographic study
    • (b) Kappe, C.O.; Fabian, W.M.F.; Semones, M.A. Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparision of ab initio semiempirical and x-ray crystallographic study. Tetrahedron 1997, 53, 2803-2816;
    • (1997) Tetrahedron , vol.53 , pp. 2803-2816
    • Kappe, C.O.1    Fabian, W.M.F.2    Semones, M.A.3
  • 18
    • 0032847541 scopus 로고    scopus 로고
    • Microwave-assisted high-speed synthesis of 4-aryl-3,4-dihydropyrimidin- 2(1H)-ones using a solventless Biginelli condensation protocol
    • (c) Kappe, C.O.; Kumar, D.; Varma, R.S. Microwave-assisted high-speed synthesis of 4-aryl-3,4-dihydropyrimidin-2(1H)-ones using a solventless Biginelli condensation protocol. Synthesis 1999, 10, 1799-1803.
    • (1999) Synthesis , vol.10 , pp. 1799-1803
    • Kappe, C.O.1    Kumar, D.2    Varma, R.S.3
  • 19
    • 0032524801 scopus 로고    scopus 로고
    • Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones
    • (a) Hu, E.H.; Sidler, D.R.; Dolling, U.H. Unprecedented catalytic three component one-pot condensation reaction: an efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones. J. Org. Chem. 1998, 63, 3454-3457;
    • (1998) J. Org. Chem. , vol.63 , pp. 3454-3457
    • Hu, E.H.1    Sidler, D.R.2    Dolling, U.H.3
  • 20
    • 0034826879 scopus 로고    scopus 로고
    • Ultrasond-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate
    • (b) Yadav, J.S.; Subba, B.V.; Reddy, K.B.; Raj, K.S.; Prasad, A.R. Ultrasond-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate. J. Chem. Soc. Perkin Trans 1, 2001, 16, 1939-1941;
    • (2001) J. Chem. Soc. Perkin Trans 1 , vol.16 , pp. 1939-1941
    • Yadav, J.S.1    Subba, B.V.2    Reddy, K.B.3    Raj, K.S.4    Prasad, A.R.5
  • 21
    • 0034674776 scopus 로고    scopus 로고
    • Lanthanide triflate catalyzed Biginelli reaction, one-pot synthesis of dihydropyrimidinones under solvent-free conditions
    • (c) Ma, Y.; Qian, C.; Wang, L.; Yang, M. Lanthanide triflate catalyzed Biginelli reaction, one-pot synthesis of dihydropyrimidinones under solvent-free conditions J. Org. Chem. 2000, 65, 3864-3868.
    • (2000) J. Org. Chem. , vol.65 , pp. 3864-3868
    • Ma, Y.1    Qian, C.2    Wang, L.3    Yang, M.4
  • 23
    • 0000865084 scopus 로고    scopus 로고
    • Iron(III) catalysis of the Michael reaction of 1,3-dicarbonyl compounds and enones
    • Christoffers, J. Iron(III) catalysis of the Michael reaction of 1,3-dicarbonyl compounds and enones. J. Chem. Commun. 1997, 10, 943-944.
    • (1997) J. Chem. Commun. , vol.10 , pp. 943-944
    • Christoffers, J.1
  • 24
    • 0002677359 scopus 로고    scopus 로고
    • Microwave-assisted oxidation of alcohols using wet alumina supported ammonium chlorochromate in solventless system
    • (a) Heravi, M.M.; Mirza-Aghayan, M.Z. Microwave-assisted oxidation of alcohols using wet alumina supported ammonium chlorochromate in solventless system. Z. Naturforsch 1998, 54b, 815-817;
    • (1998) Z. Naturforsch. , vol.54 B , pp. 815-817
    • Heravi, M.M.1    Mirza-Aghayan, M.Z.2
  • 25
    • 0033058252 scopus 로고    scopus 로고
    • Chromium trioxide on H-Y zeolite: Rapid oxidation of alcohols to carbonyl compounds in solventless system using microwaves
    • (b) Mirza-Aghayan, M.; Heravi, M.M. Chromium trioxide on H-Y zeolite: rapid oxidation of alcohols to carbonyl compounds in solventless system using microwaves. Synth. Commun. 1999, 29 (5), 785-789;
    • (1999) Synth. Commun. , vol.29 , Issue.5 , pp. 785-789
    • Mirza-Aghayan, M.1    Heravi, M.M.2
  • 27
    • 0037231862 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of the tetradentate Schiff-bases under solvent-free and catalyst-free condition
    • (d) Mirza-Aghayan, M.; Ghassemzadeh, M.; Hoseini, M.; Bolourtchian, M. Microwave-assisted synthesis of the tetradentate Schiff-bases under solvent-free and catalyst-free condition. Synth. Commun. 2003, 33 (4), 521-525.
    • (2003) Synth. Commun. , vol.33 , Issue.4 , pp. 521-525
    • Mirza-Aghayan, M.1    Ghassemzadeh, M.2    Hoseini, M.3    Bolourtchian, M.4
  • 28
    • 0036532558 scopus 로고    scopus 로고
    • Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
    • Reddy, C.V.; Mahesh, M.; Raju, P.V.K.; Babu, T.R.; Reddy, V.V.N. Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H) -ones. Tetrahedron Lett. 2002, 43, 2657-2659.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 2657-2659
    • Reddy, C.V.1    Mahesh, M.2    Raju, P.V.K.3    Babu, T.R.4    Reddy, V.V.N.5
  • 30
    • 0037054171 scopus 로고    scopus 로고
    • Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: Improved protocol condition for the Biginelli reaction
    • Fu, N.Y.; Yuan, Y.F.; Cao, Z.; Wang, S.W.; Wang, J.T.; Peppe, C. Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol condition for the Biginelli reaction. Tetrahedron 2002, 58, 4801-4807.
    • (2002) Tetrahedron , vol.58 , pp. 4801-4807
    • Fu, N.Y.1    Yuan, Y.F.2    Cao, Z.3    Wang, S.W.4    Wang, J.T.5    Peppe, C.6
  • 31
    • 0035969014 scopus 로고    scopus 로고
    • 2O-mediated three-component, one-pot, condensation reaction: An efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2-ones
    • 2O-mediated three-component, one-pot, condensation reaction: an efficient synthesis of 4-aryl-substituted 3,4-dihydropyrimidin-2- ones. Tetrahedron Lett. 2001, 42, 7873-7875.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7873-7875
    • Kumar, K.A.1    Kasthuraiah, M.2    Reddy, C.S.3    Reddy, C.D.4


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