메뉴 건너뛰기




Volumn 32, Issue 24, 2002, Pages 3703-3709

Microwave irradiation synthesis of 2-substituted benzimidazoles using PPA as a catalyst under solvent-free conditions

Author keywords

2 Substituted benzimidazoles; Microwave irradiation; Synthesis

Indexed keywords

1,2 PHENYLENEDIAMINE; BENZIMIDAZOLE DERIVATIVE; POLYPHOSPHATE;

EID: 0036937519     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120015381     Document Type: Article
Times cited : (93)

References (33)
  • 1
    • 0032927983 scopus 로고    scopus 로고
    • The effects of antirhino- and enteroviral vinylacetylene benzimidazoles on cytochrome P450 function and hepaticporphyrin levels in mice
    • (a) Tebbe, M.J.; Jensen, C.B.; Spitzer, W.A.; Franklin, R.B. The effects of antirhino- and enteroviral vinylacetylene benzimidazoles on cytochrome P450 function and hepaticporphyrin levels in mice. Antiviral Research 1999, 42(1), 25-33;
    • (1999) Antiviral Research , vol.42 , Issue.1 , pp. 25-33
    • Tebbe, M.J.1    Jensen, C.B.2    Spitzer, W.A.3    Franklin, R.B.4
  • 2
    • 0020973388 scopus 로고
    • The benzimidazole anthelmintics - Chemistry and biological activity
    • (b) Sharma, S.; Abuzar, S. The Benzimidazole Anthelmintics - Chemistry and Biological Activity. Prog. Drug. Res. 1983, 27, 85-161.
    • (1983) Prog. Drug. Res. , vol.27 , pp. 85-161
    • Sharma, S.1    Abuzar, S.2
  • 3
    • 0035072011 scopus 로고    scopus 로고
    • Novel synthetic method for precursor of muscone from tetrahydrofolate coenzyme model
    • (a) Bai, Y.; Lu, J.; Shi, Z.; Yang, B. Novel synthetic method for precursor of muscone from tetrahydrofolate coenzyme model. Synlett 2001, 544-546;
    • (2001) Synlett , pp. 544-546
    • Bai, Y.1    Lu, J.2    Shi, Z.3    Yang, B.4
  • 4
    • 0033527812 scopus 로고    scopus 로고
    • Reductive transformation of α,β-epoxy ketones and other compounds promoted through photoinduced electron transfer processes with 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI)
    • (b) Hasegawa, E.; Yoneoka, A.; Suzuki, K.; Kato, T.; Kitazume, T.; Yanagi, K. Reductive transformation of α,β-epoxy ketones and other compounds promoted through photoinduced electron transfer processes with 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI). Tetrahedron 1999, 55(45), 12957-12968;
    • (1999) Tetrahedron , vol.55 , Issue.45 , pp. 12957-12968
    • Hasegawa, E.1    Yoneoka, A.2    Suzuki, K.3    Kato, T.4    Kitazume, T.5    Yanagi, K.6
  • 5
    • 0000147025 scopus 로고    scopus 로고
    • Novel synthetic method for ketones from substituted benzimidazolium salts and grignard reagents
    • (c) Shi, Z.; Gu, H. Novel synthetic method for ketones from substituted benzimidazolium salts and grignard reagents. Science in China (Series B) 1996, 39(6), 654-660.
    • (1996) Science in China (Series B) , vol.39 , Issue.6 , pp. 654-660
    • Shi, Z.1    Gu, H.2
  • 6
    • 0001197082 scopus 로고
    • Synthesis of 4-aminobenzimidazoles and comparison of their chemical properties with those 5-aminobenzimidazoles
    • Efros, L.S. Synthesis of 4-aminobenzimidazoles and comparison of their chemical properties with those 5-aminobenzimidazoles. Zh. Obshch. Khim. 1953, 23, 957-963; Chem. Abstr. 1954, 48, 8223a.
    • (1953) Zh. Obshch. Khim. , vol.23 , pp. 957-963
    • Efros, L.S.1
  • 7
    • 4243624520 scopus 로고
    • Efros, L.S. Synthesis of 4-Aminobenzimidazoles and comparison of their chemical properties with those 5-Aminobenzimidazoles. Zh. Obshch. Khim. 1953, 23, 957-963; Chem. Abstr. 1954, 48, 8223a.
    • (1954) Chem. Abstr. , vol.48
  • 8
    • 0001560434 scopus 로고
    • The use of polyphosphoric acid in the synthesis of 2-Aryl- and 2-Alkyl-substituted benzimidazoles, benzoxazoles and benzothiazoles
    • Hein, D.W.; Alheim, R.J.; Leavitt, J.J. The use of polyphosphoric acid in the synthesis of 2-Aryl- and 2-Alkyl-substituted benzimidazoles, benzoxazoles and benzothiazoles. J. Am. Chem. Soc. 1957, 79, 427-429.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 427-429
    • Hein, D.W.1    Alheim, R.J.2    Leavitt, J.J.3
  • 9
    • 0001736767 scopus 로고
    • Synthesis of benzimidazoles for the study of their scintillating properties
    • Pushkina, L.N.; Mazalov, S.A.; Postovskii, I.Ya. Synthesis of benzimidazoles for the study of their scintillating properties. Zh. Obshch. Khim. 1962, 32, 2624-2633; Chem. Abstr. 1963, 58, 9049h.
    • (1962) Zh. Obshch. Khim. , vol.32 , pp. 2624-2633
    • Pushkina, L.N.1    Mazalov, S.A.2    Postovskii, I.Ya.3
  • 10
    • 4243437353 scopus 로고
    • Pushkina, L.N.; Mazalov, S.A.; Postovskii, I.Ya. Synthesis of Benzimidazoles for the Study of their Scintillating Properties. Zh. Obshch. Khim. 1962, 32, 2624-2633; Chem. Abstr. 1963, 58, 9049h.
    • (1963) Chem. Abstr. , vol.58
  • 11
    • 0011180507 scopus 로고
    • The modified synthetic reaction of 2-Alkylbenzimidazoles. Condensation of o-phenylenediamine with fatty acids in p-toluenesulfonic acid
    • Yoshiyuki, T.; Kazuaki, Y. The modified synthetic reaction of 2-alkylbenzimidazoles. Condensation of o-phenylenediamine with fatty acids in p-toluenesulfonic acid. Hokkaido Daigaku Kogakubu Kenkyu Hokoku 1980, 45-49; Chem. Abstr. 1980, 93, 204537k.
    • (1980) Hokkaido Daigaku Kogakubu Kenkyu Hokoku , pp. 45-49
    • Yoshiyuki, T.1    Kazuaki, Y.2
  • 12
    • 84879693117 scopus 로고
    • Yoshiyuki, T.; Kazuaki, Y. The Modified Synthetic Reaction of 2-Alkylbenzimidazoles. Condensation of o-Phenylenediamine with Fatty Acids in p-Toluenesulfonic Acid. Hokkaido Daigaku Kogakubu Kenkyu Hokoku 1980, 45-49; Chem. Abstr. 1980, 93, 204537k.
    • (1980) Chem. Abstr. , vol.93
  • 13
    • 0028140234 scopus 로고
    • Mass spectrometer as a probe in the synthesis of 2-substituted benzimidazoles
    • (a) Ramana, D.V.; Kantharaj, E. Mass spectrometer as a probe in the synthesis of 2-substituted benzimidazoles. Tetrahedron 1994, 50(8), 2485-2496;
    • (1994) Tetrahedron , vol.50 , Issue.8 , pp. 2485-2496
    • Ramana, D.V.1    Kantharaj, E.2
  • 14
    • 0016146471 scopus 로고
    • Synthesis, reactions and spectroscopic properties of benzimidazoles
    • (b) Preston, P.N. Synthesis, reactions and spectroscopic properties of benzimidazoles. Chem. Rev. 1974, 74, 279-311;
    • (1974) Chem. Rev. , vol.74 , pp. 279-311
    • Preston, P.N.1
  • 15
    • 33947458464 scopus 로고
    • The chemistry of the benzimidazoles
    • (c) Wrigth, J.B. The chemistry of the benzimidazoles. Chem. Rev. 1951, 48, 397-525.
    • (1951) Chem. Rev. , vol.48 , pp. 397-525
    • Wrigth, J.B.1
  • 16
    • 0002923552 scopus 로고
    • Synthesis of quinazolin-4-ones & benzimidazoles: Fusion of 2-aminobenzamide & 1,2-diaminobenzene with organic acids
    • Reddy, V.P.; Prasunamba, P.L.; Reddy, P.S.N.; Ratnam, C.V. Synthesis of quinazolin-4-ones & benzimidazoles: Fusion of 2-aminobenzamide & 1,2-diaminobenzene with organic acids. Indian J. Chem. 1983, 22B, 917-918.
    • (1983) Indian J. Chem. , vol.22 B , pp. 917-918
    • Reddy, V.P.1    Prasunamba, P.L.2    Reddy, P.S.N.3    Ratnam, C.V.4
  • 17
    • 0033801916 scopus 로고    scopus 로고
    • Synthetic utility of catalytic Fe(III)/Fe(II) redox cycling towards fused heterocycles: A facile accessto substituted benzimidazoles, bisbenzimidazole and imidazopyridine derivatives
    • Singh, M.P.; Sasmal, S.; Lu, W.; Chatterjee, M.N. Synthetic utility of catalytic Fe(III)/Fe(II) redox cycling towards fused heterocycles: A facile accessto substituted benzimidazoles, bisbenzimidazole and imidazopyridine derivatives. Synthesis 2000, (10), 1380-1390.
    • (2000) Synthesis , Issue.10 , pp. 1380-1390
    • Singh, M.P.1    Sasmal, S.2    Lu, W.3    Chatterjee, M.N.4
  • 18
    • 0029895141 scopus 로고    scopus 로고
    • Clay catalysis: Condensation of orthoesters with o-substituted aminoaromatics into baterocydes
    • Villemin, D.; Hammad, M.; Martin, B. Clay catalysis: Condensation of orthoesters with o-substituted aminoaromatics into baterocydes. Synth. Commun. 1996, 26(15), 2895-2899.
    • (1996) Synth. Commun. , vol.26 , Issue.15 , pp. 2895-2899
    • Villemin, D.1    Hammad, M.2    Martin, B.3
  • 21
    • 0034627373 scopus 로고    scopus 로고
    • One-pot nitro reduction-cyclisation solid phase route to benzimidazoles
    • (a) Wu, Z.; Rea, P.; Wickham, G. One-pot nitro reduction-cyclisation solid phase route to benzimidazoles. Tetrahedron Lett. 2000, 41(50), 9871-9874;
    • (2000) Tetrahedron Lett. , vol.41 , Issue.50 , pp. 9871-9874
    • Wu, Z.1    Rea, P.2    Wickham, G.3
  • 22
    • 0033588074 scopus 로고    scopus 로고
    • Solid-phase synthesis of substituted benzimidazoles
    • (b) Tumelty, D.; Schwarz, M.K.; Cao, K.; Needels, M.C. Solid-phase synthesis of substituted benzimidazoles. Tetrahedron Lett. 1999, 40(34), 6185-6188;
    • (1999) Tetrahedron Lett. , vol.40 , Issue.34 , pp. 6185-6188
    • Tumelty, D.1    Schwarz, M.K.2    Cao, K.3    Needels, M.C.4
  • 23
    • 0033515847 scopus 로고    scopus 로고
    • A new "Traceless" solid-phase synthesis strategy: Synthesis of a benzimidazole library
    • (c) Huang, W.; Scarborough, R.M. A new "Traceless" solid-phase synthesis strategy: Synthesis of a benzimidazole library. Tetrahedron Lett. 1999, 40(14), 2665-2668;
    • (1999) Tetrahedron Lett. , vol.40 , Issue.14 , pp. 2665-2668
    • Huang, W.1    Scarborough, R.M.2
  • 24
    • 0000482877 scopus 로고    scopus 로고
    • Nechlace-coded polymer-supported combinatorial synthesis of 2-arylaminobenzimidazolesl
    • (d) Smith, J.M.; Gard, J.; Cummings, W.; Kanizsai, A.; Krchnak, V.J. Nechlace-coded polymer-supported combinatorial synthesis of 2-arylaminobenzimidazolesl. Comb. Chem. 1999, 1(15), 368-370;
    • (1999) Comb. Chem. , vol.1 , Issue.15 , pp. 368-370
    • Smith, J.M.1    Gard, J.2    Cummings, W.3    Kanizsai, A.4    Krchnak, V.J.5
  • 25
    • 0032539508 scopus 로고    scopus 로고
    • Single bead IR monitoring of a novel benzimidazole synthesis
    • (e) Sun, Q.; Yan, B. Single bead IR monitoring of a novel benzimidazole synthesis. Bioorg. Med. Chem. Lett. 1998, 8(4), 361-364;
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , Issue.4 , pp. 361-364
    • Sun, Q.1    Yan, B.2
  • 26
    • 0032518765 scopus 로고    scopus 로고
    • Solid phase synthesis of 1-alkyl-2-alkylthio-5-carbamoyl-benzimidazoles
    • (f) Lee, J.; Gauthier, D.; Rivero, R.A. Solid phase synthesis of 1-alkyl-2-alkylthio-5-carbamoyl-benzimidazoles. Tetrahedron Lett. 1998, 39(3-4), 201-204.
    • (1998) Tetrahedron Lett. , vol.39 , Issue.3-4 , pp. 201-204
    • Lee, J.1    Gauthier, D.2    Rivero, R.A.3
  • 27
    • 0029078472 scopus 로고
    • Microwave assisted organic reactions
    • Caddick, S. Microwave assisted organic reactions. Tetrahedron 1995, 51(38), 10403-10432.
    • (1995) Tetrahedron , vol.51 , Issue.38 , pp. 10403-10432
    • Caddick, S.1
  • 28
    • 0033380451 scopus 로고    scopus 로고
    • Solvent-free synthesis of heterocyclic compounds using microwaves
    • For recent reviews on microwave-assisted organic reaction, see: (a) Varma, R.S. Solvent-free synthesis of heterocyclic compounds using microwaves. J. Heterocyclic Chem. 1999, 36, 1565-1571;
    • (1999) J. Heterocyclic Chem. , vol.36 , pp. 1565-1571
    • Varma, R.S.1
  • 29
    • 0033444261 scopus 로고    scopus 로고
    • Solvent-free organic synthesis
    • (b) Varma, R.S. Solvent-free organic synthesis. Green Chem. 1999, 1(1), 43-55;
    • (1999) Green Chem. , vol.1 , Issue.1 , pp. 43-55
    • Varma, R.S.1
  • 31
    • 0028956522 scopus 로고
    • Radiat. Applications of microwave-accelerated organic synthesis
    • (d) Majetich, G.; Hicks, R. Radiat. Applications of microwave-accelerated organic synthesis. Phys. Chem. 1995, 45(4), 567-579;
    • (1995) Phys. Chem. , vol.45 , Issue.4 , pp. 567-579
    • Majetich, G.1    Hicks, R.2
  • 32
    • 1842312507 scopus 로고
    • Applications of microwave energy in organic chemistry. A review
    • (e) Abramovich, R.A. Applications of Microwave Energy in Organic Chemistry. A Review. Org. Prep. Proced. Int. 1991, 23(6), 683-711.
    • (1991) Org. Prep. Proced. Int. , vol.23 , Issue.6 , pp. 683-711
    • Abramovich, R.A.1
  • 33
    • 0000724731 scopus 로고
    • 2-Alkylbenzimidazoles as derivatives for the identification of aliphatic acids
    • Pool, W.O.; Harwood, H.J.; Ralston, A.W. 2-Alkylbenzimidazoles as derivatives for the identification of aliphatic acids. J. Am. Chem. Soc. 1937, 59, 178-179.
    • (1937) J. Am. Chem. Soc. , vol.59 , pp. 178-179
    • Pool, W.O.1    Harwood, H.J.2    Ralston, A.W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.