메뉴 건너뛰기




Volumn 13, Issue 4, 2009, Pages 459-468

A reinvestigation of the acid-promoted heterocyclization of 2-(2-oxo-2-arylethyl)malononitriles in the presence of amines

Author keywords

2 (2 Oxo 2 arylethyl)malononitriles; 2 Amino 5 aryl 1 phenyl 1H pyrrole 3 carbonitriles; 2 Amino 5 arylfuran 3 (4) (di)carbonitriles; 2 Amino 5 arylfuran 3 carbonitriles; DFT; MWI; Reaction mechanism

Indexed keywords

2 (2 OXO 2 ARYLETHYL)MALONONITRILE DERIVATIVE; MALONONITRILE; UNCLASSIFIED DRUG;

EID: 70349907937     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9130-3     Document Type: Article
Times cited : (6)

References (20)
  • 1
    • 0347097718 scopus 로고
    • New syntheses of pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4-d]pyridazine, isoindolinedione and pyrazole derivatives
    • 10.1002/prac.19893310106 10.1002/prac.19893310106 1:CAS:528: DyaK3cXnslSqsQ%3D%3D
    • AO Abdelhamid AM Negm IM Abbas 1989 New syntheses of pyrazolo[3,4-d] pyrimidine, pyrazolo[3,4-d]pyridazine, isoindolinedione and pyrazole derivatives J Prakt Chem 331 31 36 10.1002/prac.19893310106 10.1002/prac.19893310106 1:CAS:528:DyaK3cXnslSqsQ%3D%3D
    • (1989) J Prakt Chem , vol.331 , pp. 31-36
    • Abdelhamid, A.O.1    Negm, A.M.2    Abbas, I.M.3
  • 2
    • 84961985847 scopus 로고    scopus 로고
    • Quantum Calculation of molecular energies and energy gradients in solution by a conductor solvent model
    • 10.1021/jp9716997 10.1021/jp9716997 1:CAS:528:DyaK1cXht1Cgt7o%3D
    • V Barone MJ Cossi 1998 Quantum Calculation of molecular energies and energy gradients in solution by a conductor solvent model Phys Chem A 102 1995 2001 10.1021/jp9716997 10.1021/jp9716997 1:CAS:528:DyaK1cXht1Cgt7o%3D
    • (1998) Phys Chem A , vol.102 , pp. 1995-2001
    • Barone, V.1    Cossi, M.J.2
  • 3
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III
    • 10.1063/1.464913 1:CAS:528:DyaK3sXisVWgtrw%3D
    • AD Becke 1993 Density-functional thermochemistry. III The role of exact exchange. J Chem Phys 98 7 5648 5652 10.1063/1.464913 1:CAS:528: DyaK3sXisVWgtrw%3D
    • (1993) The Role of Exact Exchange. J Chem Phys , vol.98 , Issue.7 , pp. 5648-5652
    • Becke, A.D.1
  • 4
    • 37449014743 scopus 로고    scopus 로고
    • Synthesis and Friedländer reaction of 5-amino-4-cyano-1,3-oxazoles
    • 10.1016/S0385-5414(07)81101-4 10.3987/COM-07-11110 1:CAS:528: DC%2BD2sXhtFansLrI
    • MC Carreiras A Eleuterio C Dias MA Brito D Brites J Marco-Contelles E Gómez-Sánchez 2007 Synthesis and Friedländer reaction of 5-amino-4-cyano-1,3-oxazoles Heterocycles 71 2249 2262 10.1016/S0385-5414(07) 81101-4 10.3987/COM-07-11110 1:CAS:528:DC%2BD2sXhtFansLrI
    • (2007) Heterocycles , vol.71 , pp. 2249-2262
    • Carreiras, M.C.1    Eleuterio, A.2    Dias, C.3    Brito, M.A.4    Brites, D.5    Marco-Contelles, J.6    Gómez-Sánchez, E.7
  • 5
    • 0003151465 scopus 로고
    • The Friedländer synthesis of quinolines
    • 1:CAS:528:DyaL38XlvVais74%3D
    • CC Cheng SJ Yan 1982 The Friedländer synthesis of quinolines Org React 28 37 201 1:CAS:528:DyaL38XlvVais74%3D
    • (1982) Org React , vol.28 , pp. 37-201
    • Cheng, C.C.1    Yan, S.J.2
  • 7
    • 33751044609 scopus 로고
    • The path of chemical reactions-the IRC approach
    • 10.1021/ar00072a001 10.1021/ar00072a001 1:CAS:528:DyaL3MXmtFSgtL0%3D
    • K Fukui 1981 The path of chemical reactions-the IRC approach Acc Chem Res 14 363 368 10.1021/ar00072a001 10.1021/ar00072a001 1:CAS:528:DyaL3MXmtFSgtL0%3D
    • (1981) Acc Chem Res , vol.14 , pp. 363-368
    • Fukui, K.1
  • 8
    • 70349913615 scopus 로고    scopus 로고
    • Gaussian Gaussian, Inc: Wallingford, CT
    • Gaussian 03 (2004) Gaussian, Inc: Wallingford, CT
    • (2004) , vol.3
  • 9
    • 1242269373 scopus 로고    scopus 로고
    • Synthesis of New Pyrrolo[2, 3-b]pyridines as a Potent Inhibitor of Tumour Necrosis Factor Alpha
    • DOI 10.1002/ardp.200300773
    • KMH Hilmy 2004 Synthesis of new pyrrolo[2,3-b]pyridines as a potent inhibitor of tumor necrosis factor alpha Arch Pharm 337 15 19 10.1002/ardp.200300773 10.1002/ardp.200300773 (Pubitemid 38222245)
    • (2004) Archiv der Pharmazie , vol.337 , Issue.1 , pp. 15-19
    • Mohammed, K.1    Hilmy, H.2
  • 10
    • 84985258737 scopus 로고
    • Nitriles in heterocyclic synthesis: A novel synthesis of 2-amino-3-pyrrolecarbonitriles
    • 10.1002/jlac.198919890285 10.1002/jlac.198919890285
    • KMH Hilmy EB Pedersen 1989 Nitriles in heterocyclic synthesis: A novel synthesis of 2-amino-3-pyrrolecarbonitriles Liebigs Ann Chem 1989 1145 1146 10.1002/jlac.198919890285 10.1002/jlac.198919890285
    • (1989) Liebigs Ann Chem , vol.1989 , pp. 1145-1146
    • Hilmy, K.M.H.1    Pedersen, E.B.2
  • 11
    • 0009305904 scopus 로고
    • Chemical transformations of α-halo ketones XX Reaction of p-substituted ω-bromoacetophenones with sodium malononitrile
    • 1:CAS:528:DyaE3cXms1eitA%3D%3D
    • VS Karavan SN Semenova AK Shchurinova 1969 Chemical transformations of α-halo ketones XX Reaction of p-substituted ω-bromoacetophenones with sodium malononitrile Zh Organicheskoi Khim 5 2161 2164 1:CAS:528: DyaE3cXms1eitA%3D%3D
    • (1969) Zh Organicheskoi Khim , vol.5 , pp. 2161-2164
    • Karavan, V.S.1    Semenova, S.N.2    Shchurinova, A.K.3
  • 13
    • 49449083916 scopus 로고    scopus 로고
    • New tacrine-dihydropyridine hybrids that inhibit acetylcholinesterase, calcium entry, and exhibit neuroprotection properties
    • references cited therein. doi:10.1016/j.bmc.2008.07.005
    • León R, de los Ríos C, Marco-Contelles J, Huertas O, Barril X, Luque FJ, López MG, García AG, Villarroya M (2008) New tacrine-dihydropyridine hybrids that inhibit acetylcholinesterase, calcium entry, and exhibit neuroprotection properties. Bioorg Med Chem 16:7759-7769. and references cited therein. doi: 10.1016/j.bmc.2008.07.005
    • (2008) Bioorg Med Chem , vol.16 , pp. 7759-7769
    • De Los Ríos, C.1    Marco-Contelles, J.2    Huertas, O.3    Barril, X.4    Fj, L.5    Mg, L.6    Ag, G.7    Villarroya, M.8    León, R.9
  • 14
    • 3042640438 scopus 로고    scopus 로고
    • 4-Acylamino-6-arylfuro[2,3-d]pyrimidines: Potent and selective glycogen synthase kinase-3 inhibitors
    • DOI 10.1016/j.bmcl.2004.05.064, PII S0960894X04007164
    • Y Maeda M Nakano H Sato Y Miyazaki SL Schweiker JL Smith AT Truesdale 2004 4-Acylamino-6-arylfuro[2,3-d]pyrimidines: potent and selective glycogen synthase kinase-3 inhibitors Bioorg Med Chem Lett 14 3907 3911 10.1016/j.bmcl.2004.05.064 15225695 10.1016/j.bmcl.2004.05.064 1:CAS:528:DC%2BD2cXlt1ehur4%3D (Pubitemid 38844393)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.15 , pp. 3907-3911
    • Maeda, Y.1    Nakano, M.2    Sato, H.3    Miyazaki, Y.4    Schweiker, S.L.5    Smith, J.L.6    Truesdale, A.T.7
  • 15
    • 85008074334 scopus 로고
    • Studies on heterocyclic enaminonitriles. VI. Synthesis of 2-amino-3-cyano-4,5-dihydrofurans
    • 1:CAS:528:DyaL2MXlt1ehur0%3D
    • T Matsuda K Yamagata Y Tomioka M Yamazaki 1985 Studies on heterocyclic enaminonitriles. VI. Synthesis of 2-amino-3-cyano-4,5-dihydrofurans Chem Pharm Bull (Tokyo) 33 937 943 1:CAS:528:DyaL2MXlt1ehur0%3D
    • (1985) Chem Pharm Bull (Tokyo) , vol.33 , pp. 937-943
    • Matsuda, T.1    Yamagata, K.2    Tomioka, Y.3    Yamazaki, M.4
  • 17
    • 34250146589 scopus 로고
    • Chemistry of s-tetracyanoethane. 2. Condensation with carbonyl compounds
    • 10.1007/BF00506605 10.1007/BF00506605
    • OE Nasakin VV Alekseev PB Terent'ev AK Bulai VA Shmorgunov 1982 Chemistry of s-tetracyanoethane. 2. Condensation with carbonyl compounds Chem Heterocycl Compd 18 1235 1240 10.1007/BF00506605 10.1007/BF00506605
    • (1982) Chem Heterocycl Compd , vol.18 , pp. 1235-1240
    • Nasakin, O.E.1    Alekseev, V.V.2    Terent'Ev, P.B.3    Bulai, A.K.4    Shmorgunov, V.A.5
  • 18
    • 29344442861 scopus 로고    scopus 로고
    • Synthesis and study of the anti-HIV activity of some polynitrile derivatives
    • 10.1007/BF02471882 10.1007/BF02471882
    • OE Nasakin PM Lukin VP Sheverdov AN Lyshchikov 1998 Synthesis and study of the anti-HIV activity of some polynitrile derivatives Pharm Chem J 32 249 251 10.1007/BF02471882 10.1007/BF02471882
    • (1998) Pharm Chem J , vol.32 , pp. 249-251
    • Nasakin, O.E.1    Lukin, P.M.2    Sheverdov, V.P.3    Lyshchikov, A.N.4
  • 19
    • 0033474569 scopus 로고    scopus 로고
    • Reactivity of β,β,γ,γ-tetracyanoalkanones, β,β-dicyanoalkanones, and 5-amino-4-cyano-2, 3-dihydrofurans
    • 1:CAS:528:DyaK1MXltV2jtbg%3D
    • OE Nasakin VP Sheverdov IV Moiseeva OV Ershov AN Chernushkin VA Tafeenko 1999 Reactivity of β,β,γ,γ-tetracyanoalkanones, β,β-dicyanoalkanones, and 5-amino-4-cyano-2, 3-dihydrofurans Russ J Gen Chem 69 291 300 1:CAS:528:DyaK1MXltV2jtbg%3D
    • (1999) Russ J Gen Chem , vol.69 , pp. 291-300
    • Nasakin, O.E.1    Sheverdov, V.P.2    Moiseeva, I.V.3    Ershov, O.V.4    Chernushkin, A.N.5    Tafeenko, V.A.6
  • 20
    • 0038243088 scopus 로고    scopus 로고
    • Modeling the reaction mechanisms of the amide hydrolysis in an N-(o-carboxybenzoyl)-L-amino acid
    • W Zhijian B Fuqiang RJ Boyd 2003 Modeling the reaction mechanisms of the amide hydrolysis in an N-(o-carboxybenzoyl)-L-amino acid J Am Chem Soc 125 6694 7000
    • (2003) J Am Chem Soc , vol.125 , pp. 6694-7000
    • Zhijian, W.1    Fuqiang, B.2    Boyd, R.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.