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Volumn 14, Issue 3, 2010, Pages 523-531

Diversity oriented heterocyclizations of pyruvic acids, aldehydes and 5-amino-N-aryl-1H-pyrazole-4-carboxamides: Catalytic and temperature control of chemoselectivity

Author keywords

5 Aminopyrazole 4 carboxamide; Microwave synthesis; Multicomponent reaction (MCR); Pyruvic acid; Selectivity; Ultrasonication

Indexed keywords

3 (2 METHOXYPHENYLCARBAMOYL) 7 P TOLYL 4,7 DIHYDROPYRAZOLO[1,5 A]PYRIMIDINE 5 CARBOXYLIC ACID; 3 (4 ETHOXYPHENYLCARBAMOYL) 7 HYDROXY 5 (4 METHOXYPHENYL) 6 PHENYL 4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDINE 7 CARBOXYLIC ACID; 3 (4 ETHOXYPHENYLCARBAMOYL) 7 HYDROXY 5,6 DIPHENYL 4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDINE 7 CARBOXYLIC ACID; 3 (4 ETHOXYPHENYLCARBAMOYL) 7 HYDROXY 6 PHENYL 5 P TOLYL 4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDINE 7 CARBOXYLIC ACID; 5 (4 CHLOROPHENYL) 3 (4 ETHOXYPHENYLCARBAMOYL) 7 HYDROXY 6 PHENYL-4,5,6,7 TETRAHYDROPYRAZOLO[1,5 A]PYRIMIDINE 7 CARBOXYLIC ACID; 5 [2 (4 CHLOROPHENYL) 4 HYDROXY 5 OXO 3 PHENYL 2,5 DIHYDRO 1H PYRROL 1 YL]N(4 ETHOXYPHENYL) 1H PYRAZOLE 4 CARBOXAMIDE; 5 [5 (4 CHLOROPHENYL) 2 OXO 2,5 DIHYDROFURAN 3 YLAMINO) N (4 ETHOXYPHENYL) 1H PYRAZOLE 4 CARBOXAMIDE; 5 [5 (4 CHLOROPHENYL) 2 OXO 2,5 DIHYDROFURAN 3 YLAMINO)N P TOLYL 1H PYRAZOLE 4 CARBOXAMIDE; 5S [5 (4 CHLOROPHENYL) 2 OXO 2,5 DIHYDROFURAN 3 YLAMINO)N(4 FLUOROPHENYL) 1H PYRAZOLE 4 CARBOXAMIDE; 7 (4 CHLOROPHENYL) 3 (P TOLYLCARBAMOYL) 4,7 DIHYDROPYRAZOLO[1,5 A]PYRIMIDINE 5 CARBOXYLIC ACID; ALDEHYDE; AMIDE; N (4 FLUOROPHENYL) 5 (2 OXO 5 P TOLYL 2,5 DIHYDROFURAN 3 YLAMINO)1H PYRAZOLE 4 CARBOXAMIDE; N(4 ETHOXYPHENYL) 5 (3 HYDROXY 2 OXO 4 PHENYL 5 P TOLYL 2,5 DIHYDRO 1H PYRROL 1 YL) 1H PYRAZOLE 4 CARBOXAMIDE; N(4 ETHOXYPHENYL) 5 (3 HYDROXY 2 OXO 4,5 DIPHENYL 2,5 DIHYDRO 1H PYRROL 1 YL) 1H PYRAZOLE 4 CARBOXAMIDE; N(4 ETHOXYPHENYL) 5 (3 HYDROXY 5 (4 METHOXYPHENYL) 2 OXO 4 PHENYL 2,5 DIHYDRO 1H PYRROL 1 YL) 1H PYRAZOLE 4 CARBOXAMIDE; PYRUVIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 78650174836     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-010-9226-9     Document Type: Article
Times cited : (35)

References (26)
  • 3
    • 84890597202 scopus 로고    scopus 로고
    • J. Zhu H. Bienaymé (eds). Weinheim Wiley-VCH
    • Zhu, J, Bienaymé, H (eds) (2005) Multicomponent reactions. Weinheim, Wiley-VCH
    • (2005) Multicomponent Reactions
  • 4
    • 65249100749 scopus 로고    scopus 로고
    • Strategies for innovation in multicomponent reaction design
    • 10.1021/ar800214s 1:CAS:528:DC%2BD1MXhtV2ltL4%3D 10.1021/ar800214s 19175315
    • B Ganem 2009 Strategies for innovation in multicomponent reaction design Acc Chem Res 42 463 472 10.1021/ar800214s 1:CAS:528:DC%2BD1MXhtV2ltL4%3D 10.1021/ar800214s 19175315
    • (2009) Acc Chem Res , vol.42 , pp. 463-472
    • Ganem, B.1
  • 5
    • 60749120878 scopus 로고    scopus 로고
    • Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds
    • 10.1002/chem.200802140 1:CAS:528:DC%2BD1MXhsl2ht7Y%3D 10.1002/chem.200802140
    • JD Sunderhaus SF Martin 2009 Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds Chem Eur J 15 1300 1308 10.1002/chem.200802140 1:CAS:528:DC%2BD1MXhsl2ht7Y%3D 10.1002/chem.200802140
    • (2009) Chem Eur J , vol.15 , pp. 1300-1308
    • Sunderhaus, J.D.1    Martin, S.F.2
  • 6
    • 55849150974 scopus 로고    scopus 로고
    • 1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles
    • doi: 10.1039/b809206k
    • Groenendaal B, Ruijter E, Orru RVA (2008) 1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles. Chem Comm 5474-5489. doi: 10.1039/b809206k
    • (2008) Chem Comm , pp. 5474-5489
    • Groenendaal, B.1    Ruijter, E.2    Rva, O.3
  • 7
    • 33846895846 scopus 로고    scopus 로고
    • A. Loupy (eds). Weinheim Wiley-VCH
    • Loupy, A (eds) (2006) Microwaves in organic synthesis. Weinheim, Wiley-VCH
    • (2006) Microwaves in Organic Synthesis
  • 9
    • 62649143644 scopus 로고    scopus 로고
    • Microwave enhanced synthesis
    • 10.1016/j.tet.2009.01.105 1:CAS:528:DC%2BD1MXjsl2htro%3D 10.1016/j.tet.2009.01.105
    • S Caddick R Fitzmaurice 2009 Microwave enhanced synthesis Tetrahedron 65 3325 3355 10.1016/j.tet.2009.01.105 1:CAS:528:DC%2BD1MXjsl2htro%3D 10.1016/j.tet.2009.01.105
    • (2009) Tetrahedron , vol.65 , pp. 3325-3355
    • Caddick, S.1    Fitzmaurice, R.2
  • 10
    • 0002740049 scopus 로고    scopus 로고
    • Ultrasound as a new tool for synthetic chemists
    • R. van Eldick C.D. Hubbard (eds). Wiley Stony Brook
    • Mason TJ, Luche J-L (1997) Ultrasound as a new tool for synthetic chemists. In: van Eldick R, Hubbard CD (eds) Chemistry under extreme or non-classical conditions. Wiley, Stony Brook, pp 317-380
    • (1997) Chemistry under Extreme or Non-classical Conditions , pp. 317-380
    • Mason, T.J.1    Luche, J.-L.2
  • 11
    • 33645222276 scopus 로고    scopus 로고
    • Power ultrasound in organic synthesis: Moving cavitational chemistry from academia to innovative and large-scale applications
    • DOI 10.1039/b503848k
    • G Cravotto PJ Cintas 2006 Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications Chem Soc Rev 35 180 196 10.1039/b503848k 1:CAS:528:DC%2BD28Xot1ajsQ%3D%3D 10.1039/b503848k 16444299 (Pubitemid 43485008)
    • (2006) Chemical Society Reviews , vol.35 , Issue.2 , pp. 180-196
    • Cravotto, G.1    Cintas, P.2
  • 12
    • 60749129757 scopus 로고    scopus 로고
    • Ultrasound in heterocycles chemistry
    • 10.1016/j.tet.2008.12.027 1:CAS:528:DC%2BD1MXisVOitLc%3D 10.1016/j.tet.2008.12.027
    • R Cella HA Stefani 2009 Ultrasound in heterocycles chemistry Tetrahedron 65 2619 2641 10.1016/j.tet.2008.12.027 1:CAS:528:DC%2BD1MXisVOitLc%3D 10.1016/j.tet.2008.12.027
    • (2009) Tetrahedron , vol.65 , pp. 2619-2641
    • Cella, R.1    Stefani, H.A.2
  • 13
    • 0004145285 scopus 로고    scopus 로고
    • P. Wasserscheid T. Welton (eds). Wiley-VCH Weinheim
    • Wasserscheid, P, Welton, T (eds) (2007) Ionic liquids in synthesis. Wiley-VCH, Weinheim
    • (2007) Ionic Liquids in Synthesis
  • 16
    • 33845747238 scopus 로고    scopus 로고
    • Cyclocondensation reactions of 5-aminopyrazoles, pyruvic acids and aldehydes. Multicomponent approaches to pyrazolopyridines and related products
    • DOI 10.1016/j.tet.2006.11.048, PII S0040402006018497
    • VA Chebanov YI. Sakhno SM Desenko VN Chernenko VI Musatov SV Shishkina OV Shishkin CO Kappe 2007 Cyclocondensation reactions of 5-aminopyrazoles, pyruvic acids and aldehydes. Multicomponent approaches to pyrazolopyridines and related products Tetrahedron 63 1229 1242 10.1016/j.tet.2006.11.048 1:CAS:528:DC%2BD2sXis1ah 10.1016/j.tet.2006.11.048 (Pubitemid 44970485)
    • (2007) Tetrahedron , vol.63 , Issue.5 , pp. 1229-1242
    • Chebanov, V.A.1    Sakhno, Y.I.2    Desenko, S.M.3    Chernenko, V.N.4    Musatov, V.I.5    Shishkina, S.V.6    Shishkin, O.V.7    Kappe, C.O.8
  • 19
    • 46849121202 scopus 로고    scopus 로고
    • Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes
    • DOI 10.1021/jo800825c
    • VA Chebanov VE Saraev SM Desenko VN Chernenko IV Knyazeva U Groth T Glasnov CO Kappe 2008 Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone and aldehydes J Org Chem 73 5110 5118 10.1021/jo800825c 1:CAS:528:DC%2BD1cXms1GitLw%3D 10.1021/jo800825c 18512991 (Pubitemid 351956576)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.13 , pp. 5110-5118
    • Chebanov, V.A.1    Saraev, V.E.2    Desenko, S.M.3    Chernenko, V.N.4    Knyazeva, I.V.5    Groth, U.6    Glasnov, T.N.7    Kappe, C.O.8
  • 20
    • 85047340114 scopus 로고    scopus 로고
    • Multicomponent cyclocondensation reactions of aminoazoles, arylpyruvic acids and aldehydes with controlled chemoselectivity
    • 10.1016/j.tet.2008.09.089 1:CAS:528:DC%2BD1cXhtlWlsbnE 10.1016/j.tet.2008.09.089
    • YI Sakhno SM Desenko SV Shishkina OV Shishkin DO Sysoyev U Groth CO Kappe VA Chebanov 2008 Multicomponent cyclocondensation reactions of aminoazoles, arylpyruvic acids and aldehydes with controlled chemoselectivity Tetrahedron 64 11041 11049 10.1016/j.tet.2008.09.089 1:CAS:528:DC%2BD1cXhtlWlsbnE 10.1016/j.tet.2008.09.089
    • (2008) Tetrahedron , vol.64 , pp. 11041-11049
    • Sakhno, Y.I.1    Desenko, S.M.2    Shishkina, S.V.3    Shishkin, O.V.4    Sysoyev, D.O.5    Groth, U.6    Kappe, C.O.7    Chebanov, V.A.8
  • 21
    • 67650072566 scopus 로고    scopus 로고
    • Chemoselectivity of multicomponent condensations of barbituric acids, 5-aminopyrazoles and aldehydes
    • 10.1055/s-0028-1088024 10.1055/s-0028-1088024
    • EA Muravyova SV Shishkina VI Musatov OV Shishkin SM Desenko VA Chebanov 2009 Chemoselectivity of multicomponent condensations of barbituric acids, 5-aminopyrazoles and aldehydes Synthesis 2009 1375 1385 10.1055/s-0028-1088024 10.1055/s-0028-1088024
    • (2009) Synthesis , vol.2009 , pp. 1375-1385
    • Muravyova, E.A.1    Shishkina, S.V.2    Musatov, V.I.3    Shishkin, O.V.4    Desenko, S.M.5    Chebanov, V.A.6
  • 23
    • 4744341276 scopus 로고    scopus 로고
    • Enantioselective synthesis of non-natural amino acids using phenylalanine dehydrogenases modified by site-directed mutagenesis
    • 10.1039/B406364C 1:CAS:528:DC%2BD2cXnt1Grsrc%3D 10.1039/b406364c 15351834
    • P Busca F Paradisi E Moynihan AR Maguire PC Engel 2004 Enantioselective synthesis of non-natural amino acids using phenylalanine dehydrogenases modified by site-directed mutagenesis Org Biomol Chem 2 2684 2691 10.1039/B406364C 1:CAS:528:DC%2BD2cXnt1Grsrc%3D 10.1039/b406364c 15351834
    • (2004) Org Biomol Chem , vol.2 , pp. 2684-2691
    • Busca, P.1    Paradisi, F.2    Moynihan, E.3    Maguire, A.R.4    Engel, P.C.5
  • 24
    • 0000841653 scopus 로고
    • Mono-alkylation of sodium 5-aminotetrazole in aqueous medium
    • 10.1021/ja01632a094 1:CAS:528:DyaG2MXls1KrtA%3D%3D 10.1021/ja01632a094
    • RA Henry WG Finnegan 1954 Mono-alkylation of sodium 5-aminotetrazole in aqueous medium J Am Chem Soc 76 923 926 10.1021/ja01632a094 1:CAS:528: DyaG2MXls1KrtA%3D%3D 10.1021/ja01632a094
    • (1954) J Am Chem Soc , vol.76 , pp. 923-926
    • Henry, R.A.1    Finnegan, W.G.2
  • 25
    • 0001343068 scopus 로고
    • Synthese von Benzylidenaminopyrazolen und Bispyrazolopyridinen
    • 10.1002/prac.19903320312 1:CAS:528:DyaK3cXmtlWhtLo%3D 10.1002/prac.19903320312
    • L Hennig J Hofmann M Alva-Astudillo G Mann 1990 Synthese von Benzylidenaminopyrazolen und Bispyrazolopyridinen J Prakt Chem 332 351 358 10.1002/prac.19903320312 1:CAS:528:DyaK3cXmtlWhtLo%3D 10.1002/prac.19903320312
    • (1990) J Prakt Chem , vol.332 , pp. 351-358
    • Hennig, L.1    Hofmann, J.2    Alva-Astudillo, M.3    Mann, G.4
  • 26
    • 37549039510 scopus 로고    scopus 로고
    • A short history of SHELX
    • 10.1107/S0108767307043930 10.1107/S0108767307043930 18156677
    • GM Sheldrick 2008 A short history of SHELX Acta Crystallogr A 64 112 122 10.1107/S0108767307043930 10.1107/S0108767307043930 18156677
    • (2008) Acta Crystallogr A , vol.64 , pp. 112-122
    • Sheldrick, G.M.1


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