How to cite this paper
Thakare, M., Shaikh, R & Tayade, D. (2020). Catalyst-free synthesis of 1,2-disubstituted benzimidazoles in aqueous media using oxygen as the oxidant.Current Chemistry Letters, 9(2), 63-70.
Refrences
1. Spasov A. A., Yozhitsa I. N. (1999) Benzimidazole derivatives: Spectrum of pharmacological activity and toxicological properties. J. Pharma. Chem., 33 (6) 232-243.
2. Horton D. A., Bourne G. T., Smythe M. L. (2003) The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures. Chem. Rev., 103 (3) 893-930.
3. Alkahtani H. M., Abbas A. Y., Wang S. D. (2012) Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents. Biorg. Med. Chem. Lett., 22 (3) 1317-1321.
4. Fang B., Zhou, C. H., Rao X. C. (2010) Synthesis and biological activities of novel amine-derived bis-azoles as potential antibacterial and antifungal agents. Eur. J. Med. Chem., 45 (10) 4388-4389.
5. Braun S., Botzki A., Salmen S., Textor C., Bernhardt G., Dove S., Buschauer A. (2011) Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronanlyase. Eur. J. Med. Chem., 46 (9) 4419-4429.
6. Tipparaju S. K., Joyasawal S., Pieroni M., Kaiser M., Brun R., Kozikowski A. P. (2008) In Pursuit of Natural Product Leads: Synthesis and Biological Evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxylic acid (A-33853) and Its Analogues: Discovery of N-(2-Benzoxazol-2-ylphenyl)benzamides as Novel Antileishmanial Chemotypes. J. Med. Chem., 51 (23) 7344-7347.
7. Moore T. W., Sana K., Yan D., Krumm S. A., Thepchatri P., Snyder J. P., Marengo J., Arrendale R. F., Prussia A. J., Natchus M. G., Liotta D. C., Plemper R. K., Sun A. (2013) Synthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy. ACS Med. Chem. Lett., 4 (8) 762-767.
8. Rida S. M., Ashour F. A., El-Hawash S. A. M., Elsemary M. M., Badr M. H., Shalaby M. A. (2005) Synthesis of some novel benzoxazole derivatives as anticancer, anti-HIV-1 and antimicrobial agentsSynthesis, Antiinflammatory and Antibacterial Activities of Substituted Phenyl Benzimidazoles. Eur. J. Med. Chem., 40 (9) 949-959.
9. Leonard J T., Rajesh O. S., Jeyaseeli L., Murugesh K., Sivakumar R., Gunasekaran V. (2007) Synthesis, Antiinflammatory and Antibacterial Activities of Substituted Phenyl Benzimidazoles. Asian J. Chem., 19 (1) 116-120.
10 Pal S., Hwang W. –S., Lin I. J. B., Lee C. –S. (2007) Benzene benzimidazole containing Pd(II) metallacycle: Synthesis, X-ray crystallographic characterization and its use as an efficient Suzuki coupling catalyst. J. Mol. Catal. A.: Chem., 269 (1-2) 197-203.
11 Rajadhyaksha D. D., Rangnekar D. W. (1986) Synthesis of pyrazolo[4′,3′:5,6]pyrido[1,2-a]benzimidazole derivatives and study of their fluorescence properties. J. Chem. Technol. Biotechnol., 36 (7) 300-304.
12 Asensio J. A., Gomez-Romero P. (2005) Recent Developments on Proton Conduc-ting Poly(2,5-benzimidazole) (ABPBI) Membranes for High Temperature Poly-mer Electrolyte Membrane Fuel Cell. Fuel Cells, 5 (3) 336-343.
13 Das B., Holla H., Srinivas Y. (2007) Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazoles. Tetrahedron Lett., 48 (6) 61-64.
14 Chang J. B., Zhao K., Pan S. (2002) Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases—a solution-phase strategy for library synthesis. Tetrahedron Lett., 43 (6) 951-954.
15 Liu M. R., Li H. L. (2012) TEMPO-mediated oxidation of unbleached bagasse pulp. Advanced Materials Research, 496, 71-74.
16 Chen Y. X., Qian L. F., Zhang W., Han B. (2008) Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO. Angew. Chem. Int. Ed., 47 (48) 9330-9333.
17 Hein D. W., Alheim R. J., Leavitt J. J. (1957) The Use of Polyphosphoric Acid in the Synthesis of 2-Aryl- and 2-Alkyl-substituted Benzimidazoles, Benzoxazoles and Benzothiazoles. J. Am. Chem. Soc., 79 (2) 427-429.
18 Terashima M., Ishii M., Kanaoka Y. (1982) A facile synthesis of 2-substituted benzoxazoles. Synthesis, 484-485.
19 Wright J. B. (1951) The chemistry of the benzimidazoles. Chem. Rev., 48 (3) 397–541.
20 (a) Tidwell R. R., Geratz J. D., Dann O., Volz G., Zeh D., Loewe H. (1978) Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases. J. Med. Chem., 21 (7) 613–623; (b) Fairley T. A., Tidwell R. R., Donkor I., Naiman, N. A., Ohemeng K. A., Lombardy R. J., Bentley J. A., Cory B. M. (1993) Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles). Med. Chem., 36 (12) 1746–1753.
21 Bourgrin K., Loupy A., Soufiaoui M. (1998) Troisnouvellesvoies de synthèse des dérivés 1,3-azoliques sous micro-ondes. Tetrahedron, 54 (28) 8055–8064.
22 Harapanhalli R. S., McLaughlin L. W., Howell R. W., Rao D. V., Adelstein S. J., Kassis A. I. (1996) [125I/127I]IodoHoechst 33342: Synthesis, DNA Binding, and Biodistribution. J. Med. Chem., 39 (24) 4804–4809.
23 Verner E., Katz B. A., Spencer, J. R. Allen D., Hataye J., Hruzewicz, W., Hui, H. C., Kolesnikov A., Li Y., Luong C., Martelli A., Radika K., Rai R., She M., Shrader W., Sprengeler P. A., Trapp S., Wang J., Young W. B., Mackman R. L. (2001) Development of serine protease inhibitors displaying a multicentered short (<2.3 Å) hydrogen bond binding mode: inhibitors of urokinase-type plasminogen activator and factor Xa. J. Med. Chem., 44 (17) 2753–2771.
24 Vanden Eynde J. J., Delfosse F., Lor P., Van Haverbeke Y. (1995) .2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, a mild catalyst for the formation of carbon-nitrogen bonds. Tetrahedron, 51 (20) 5813–5818.
25 Patzold F., Zeuner F., Heyer Th., Niclas H.-J. (1992) Dehydrogenations using benzofuroxan as oxidant. Synth. Commun., 22 281–284.
26 Bhatnagar I., George M. V. (1968) Oxidation with metal oxides—II : Oxidation of chalconephenylhydrazones, pyrazolines, o-aminobenzylidineanils and o-hydroxybenzylidineanils with manganese dioxide. Tetrahedron, 24 1293–1298.
27 Stephens F. F., Bower J. D. (1949) The preparation of benziminazoles and benzoxazoles from Schiff's bases. PartI. J. Chem. Soc., 2971–2972.
28 Beaulieu P. L., Hache B., von Moos E. A. (2003) A practical oxone®-mediated, high-throughput, solution-phase synthesis of benzimidazoles from 1,2-phenylenediamines and aldehydes and its application to preparative scale synthesis. Synthesis, 11 1683–1692.
29 Austen S. C., Kane J. M. (2001) A short synthesis of the parp inhibitor 2-(4-trifluoro-methylphenyl)benzimidazole-4-carboxamide (NU1077). J. Heterocycl. Chem., 38 (4) 979–980.
30 Lombardy R. L., Tanious F. A., Ramachandran K., Tidwell R. R., Wilson W. D. (1996) Synthesis and DNA Interactions of BenzimidazoleDications Which Have Activity against Opportunistic Infections. J. Med. Chem., 39 (7) 1452–1462.
31 Lin S., Yang L. H. (2005) A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant. Tetrahedron Lett., 46 (25) 4315–4319.
32 Saggiomo V., Lüning U. (2009) On the formation of imines in water—a comparison. Tetrahedron Lett., 50 (32) 4663-4665.
33 Sharghi H., Asemani O., Khalifeh R. (2008) New one‐pot procedure for the synthesis of 2‐substituted benzimidazoles. Synth. Commun., 38 (7) 1128-1136.
34 Thakare M. P., Shaikh R., Thakare A. (2016) Synthesis, characterization and evaluation of antimicrobial activity of novel chiral benzimidazoles. Chemistry & Biology Interface, 6 (5) 327-332.
2. Horton D. A., Bourne G. T., Smythe M. L. (2003) The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures. Chem. Rev., 103 (3) 893-930.
3. Alkahtani H. M., Abbas A. Y., Wang S. D. (2012) Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents. Biorg. Med. Chem. Lett., 22 (3) 1317-1321.
4. Fang B., Zhou, C. H., Rao X. C. (2010) Synthesis and biological activities of novel amine-derived bis-azoles as potential antibacterial and antifungal agents. Eur. J. Med. Chem., 45 (10) 4388-4389.
5. Braun S., Botzki A., Salmen S., Textor C., Bernhardt G., Dove S., Buschauer A. (2011) Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronanlyase. Eur. J. Med. Chem., 46 (9) 4419-4429.
6. Tipparaju S. K., Joyasawal S., Pieroni M., Kaiser M., Brun R., Kozikowski A. P. (2008) In Pursuit of Natural Product Leads: Synthesis and Biological Evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxylic acid (A-33853) and Its Analogues: Discovery of N-(2-Benzoxazol-2-ylphenyl)benzamides as Novel Antileishmanial Chemotypes. J. Med. Chem., 51 (23) 7344-7347.
7. Moore T. W., Sana K., Yan D., Krumm S. A., Thepchatri P., Snyder J. P., Marengo J., Arrendale R. F., Prussia A. J., Natchus M. G., Liotta D. C., Plemper R. K., Sun A. (2013) Synthesis and Metabolic Studies of Host-Directed Inhibitors for Antiviral Therapy. ACS Med. Chem. Lett., 4 (8) 762-767.
8. Rida S. M., Ashour F. A., El-Hawash S. A. M., Elsemary M. M., Badr M. H., Shalaby M. A. (2005) Synthesis of some novel benzoxazole derivatives as anticancer, anti-HIV-1 and antimicrobial agentsSynthesis, Antiinflammatory and Antibacterial Activities of Substituted Phenyl Benzimidazoles. Eur. J. Med. Chem., 40 (9) 949-959.
9. Leonard J T., Rajesh O. S., Jeyaseeli L., Murugesh K., Sivakumar R., Gunasekaran V. (2007) Synthesis, Antiinflammatory and Antibacterial Activities of Substituted Phenyl Benzimidazoles. Asian J. Chem., 19 (1) 116-120.
10 Pal S., Hwang W. –S., Lin I. J. B., Lee C. –S. (2007) Benzene benzimidazole containing Pd(II) metallacycle: Synthesis, X-ray crystallographic characterization and its use as an efficient Suzuki coupling catalyst. J. Mol. Catal. A.: Chem., 269 (1-2) 197-203.
11 Rajadhyaksha D. D., Rangnekar D. W. (1986) Synthesis of pyrazolo[4′,3′:5,6]pyrido[1,2-a]benzimidazole derivatives and study of their fluorescence properties. J. Chem. Technol. Biotechnol., 36 (7) 300-304.
12 Asensio J. A., Gomez-Romero P. (2005) Recent Developments on Proton Conduc-ting Poly(2,5-benzimidazole) (ABPBI) Membranes for High Temperature Poly-mer Electrolyte Membrane Fuel Cell. Fuel Cells, 5 (3) 336-343.
13 Das B., Holla H., Srinivas Y. (2007) Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazoles. Tetrahedron Lett., 48 (6) 61-64.
14 Chang J. B., Zhao K., Pan S. (2002) Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases—a solution-phase strategy for library synthesis. Tetrahedron Lett., 43 (6) 951-954.
15 Liu M. R., Li H. L. (2012) TEMPO-mediated oxidation of unbleached bagasse pulp. Advanced Materials Research, 496, 71-74.
16 Chen Y. X., Qian L. F., Zhang W., Han B. (2008) Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO. Angew. Chem. Int. Ed., 47 (48) 9330-9333.
17 Hein D. W., Alheim R. J., Leavitt J. J. (1957) The Use of Polyphosphoric Acid in the Synthesis of 2-Aryl- and 2-Alkyl-substituted Benzimidazoles, Benzoxazoles and Benzothiazoles. J. Am. Chem. Soc., 79 (2) 427-429.
18 Terashima M., Ishii M., Kanaoka Y. (1982) A facile synthesis of 2-substituted benzoxazoles. Synthesis, 484-485.
19 Wright J. B. (1951) The chemistry of the benzimidazoles. Chem. Rev., 48 (3) 397–541.
20 (a) Tidwell R. R., Geratz J. D., Dann O., Volz G., Zeh D., Loewe H. (1978) Diarylamidine derivatives with one or both of the aryl moieties consisting of an indole or indole-like ring. Inhibitors of arginine-specific esteroproteases. J. Med. Chem., 21 (7) 613–623; (b) Fairley T. A., Tidwell R. R., Donkor I., Naiman, N. A., Ohemeng K. A., Lombardy R. J., Bentley J. A., Cory B. M. (1993) Structure, DNA minor groove binding, and base pair specificity of alkyl- and aryl-linked bis(amidinobenzimidazoles) and bis(amidinoindoles). Med. Chem., 36 (12) 1746–1753.
21 Bourgrin K., Loupy A., Soufiaoui M. (1998) Troisnouvellesvoies de synthèse des dérivés 1,3-azoliques sous micro-ondes. Tetrahedron, 54 (28) 8055–8064.
22 Harapanhalli R. S., McLaughlin L. W., Howell R. W., Rao D. V., Adelstein S. J., Kassis A. I. (1996) [125I/127I]IodoHoechst 33342: Synthesis, DNA Binding, and Biodistribution. J. Med. Chem., 39 (24) 4804–4809.
23 Verner E., Katz B. A., Spencer, J. R. Allen D., Hataye J., Hruzewicz, W., Hui, H. C., Kolesnikov A., Li Y., Luong C., Martelli A., Radika K., Rai R., She M., Shrader W., Sprengeler P. A., Trapp S., Wang J., Young W. B., Mackman R. L. (2001) Development of serine protease inhibitors displaying a multicentered short (<2.3 Å) hydrogen bond binding mode: inhibitors of urokinase-type plasminogen activator and factor Xa. J. Med. Chem., 44 (17) 2753–2771.
24 Vanden Eynde J. J., Delfosse F., Lor P., Van Haverbeke Y. (1995) .2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, a mild catalyst for the formation of carbon-nitrogen bonds. Tetrahedron, 51 (20) 5813–5818.
25 Patzold F., Zeuner F., Heyer Th., Niclas H.-J. (1992) Dehydrogenations using benzofuroxan as oxidant. Synth. Commun., 22 281–284.
26 Bhatnagar I., George M. V. (1968) Oxidation with metal oxides—II : Oxidation of chalconephenylhydrazones, pyrazolines, o-aminobenzylidineanils and o-hydroxybenzylidineanils with manganese dioxide. Tetrahedron, 24 1293–1298.
27 Stephens F. F., Bower J. D. (1949) The preparation of benziminazoles and benzoxazoles from Schiff's bases. PartI. J. Chem. Soc., 2971–2972.
28 Beaulieu P. L., Hache B., von Moos E. A. (2003) A practical oxone®-mediated, high-throughput, solution-phase synthesis of benzimidazoles from 1,2-phenylenediamines and aldehydes and its application to preparative scale synthesis. Synthesis, 11 1683–1692.
29 Austen S. C., Kane J. M. (2001) A short synthesis of the parp inhibitor 2-(4-trifluoro-methylphenyl)benzimidazole-4-carboxamide (NU1077). J. Heterocycl. Chem., 38 (4) 979–980.
30 Lombardy R. L., Tanious F. A., Ramachandran K., Tidwell R. R., Wilson W. D. (1996) Synthesis and DNA Interactions of BenzimidazoleDications Which Have Activity against Opportunistic Infections. J. Med. Chem., 39 (7) 1452–1462.
31 Lin S., Yang L. H. (2005) A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant. Tetrahedron Lett., 46 (25) 4315–4319.
32 Saggiomo V., Lüning U. (2009) On the formation of imines in water—a comparison. Tetrahedron Lett., 50 (32) 4663-4665.
33 Sharghi H., Asemani O., Khalifeh R. (2008) New one‐pot procedure for the synthesis of 2‐substituted benzimidazoles. Synth. Commun., 38 (7) 1128-1136.
34 Thakare M. P., Shaikh R., Thakare A. (2016) Synthesis, characterization and evaluation of antimicrobial activity of novel chiral benzimidazoles. Chemistry & Biology Interface, 6 (5) 327-332.