One-Pot Efficient Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-Triaryl-1H-imidazoles Using Oxalic Acid Catalyst

Nagnnath D. Kokare; Jaiprakash N. Sangshetti; Devanand B. Shinde

doi:10.1055/s-2007-983872

PAPER

One-Pot Efficient Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-Triaryl-1H-imidazoles Using Oxalic Acid Catalyst

Nagnnath D. Kokare^a,b, Jaiprakash N. Sangshetti^a, Devanand B. Shinde^a
^a Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004 (MS), India
^b New Drug Discovery, Wockhardt Research Centre, Aurangabad-431210 (MS), India
e-Mail: dbschemtech@hotmail.com;

Abstract

All articles of this category

Abstract

Oxalic acid was found to be a versatile catalyst for the synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2-aryl-4,5-diphenyl-1H-imidazoles in moderate to excellent isolated yields. 2-Aryl-1-arylmethyl-1H-benzimidazoles were efficiently synthesized from o-phenylenediamine and various substituted aldehydes using 10 mol% oxalic acid. 2-Aryl-4,5-diphenyl-1H-imidazoles were synthesized from benzil or benzoin, ammonium acetate, and aromatic aldehydes. The advantages of this method are the use of an inexpensive and readily available catalyst, easy workup, and improved yields, and the use of an ethanol-water solvent that is considered to be relatively environmentally benign.

Key words

oxalic acid - 2-aryl-1-arylmethyl-1H-benzimidazole - 2,4,5-triaryl-1H-imidazole - benzoin - benzil - aromatic aldehydes

Full Text

References

<A NAME="RZ06307SS-1A">1a</A> Tamm I. Sehgal PB. Adv. Virus Res. 1978, 22: 187

<A NAME="RZ06307SS-1B">1b</A> Tamm I. Science 1957, 126: 1235

<A NAME="RZ06307SS-1C">1c</A> Tebbe MJ. Spitzer WA. Victor F. Miller SC. Lee CC. Sattelberg TR. McKinney E. Tang JC. J. Med. Chem. 1997, 40: 3937

<A NAME="RZ06307SS-1D">1d</A> Migawa MT. Giradet JL. Walker JA. Koszalka GW. Chamberlain SD. Drach JC. Townsend LB. J. Med. Chem. 1998, 41: 1242

<A NAME="RZ06307SS-1E">1e</A> Porcari AR. Devivar RV. Kucera LS. Drach JC. Townsend LB. J. Med. Chem. 1998, 41: 1252

<A NAME="RZ06307SS-2A">2a</A> Grimmett MR. Imidazole and Benzimidazole Synthesis Acadamic Press; San Diego: 1997.

<A NAME="RZ06307SS-2B">2b</A> Roth M. Morningstar ML. Boyer PL. Hughes SH. Buckheit RW. Michejda CJ. J. Med. Chem. 1997, 40, 4199

<A NAME="RZ06307SS-3">3</A> Figge A. Altenbach HJ. Brauer DJ. Tielmann P. Tetrahedron: Asymmetry 2002, 13: 137

<A NAME="RZ06307SS-4A">4a</A> Dudd LM. Venardou E. Gaircia-Verdugo E. Licence P. Blake AJ. Wilson C. Poliakoff M. Green Chem. 2003, 5: 187

<A NAME="RZ06307SS-4B">4b</A> Preston PN. In The Chemistry of Heterocyclic Compounds Vol. 40: Weissberger A. Taylor EC. John Wiley; New York: 1981.

<A NAME="RZ06307SS-4C">4c</A> Huang W. Scarborough RM. Tetrahedron Lett. 1999, 40: 2665

<A NAME="RZ06307SS-4D">4d</A> Chi Y.-C. Sun C.-M. Synlett 2000, 591

<A NAME="RZ06307SS-4E">4e</A> Bougrin K. Soufiaoui M. Tetrahedron Lett. 1995, 36: 3683

<A NAME="RZ06307SS-5A">5a</A> Perry RJ. Wilson BD. J. Org. Chem. 1993, 58: 7016

<A NAME="RZ06307SS-5B">5b</A> Brain CT. Brunton SA. Tetrahedron Lett. 2002, 43: 1893

<A NAME="RZ06307SS-5C">5c</A> Konig W. Gieger R. Chem. Ber. 1970, 103: 788

<A NAME="RZ06307SS-6A">6a</A> Sun WH. Shao SH. Chen Y. Hu HM. Sheldon RA. Wang HG. Leng XB. Jin XL. Organometallics 2002, 21: 4350

<A NAME="RZ06307SS-6B">6b</A> Ben-alloum A. Bakkas S. Soufiaoui M. Tetrahedron Lett. 1998, 39: 4481

<A NAME="RZ06307SS-7A">7a</A> Nagata K. Itoh T. Ishikawa H. Ohsawa A. Heterocycles 2003, 61: 93

<A NAME="RZ06307SS-7B">7b</A> Currini M. Epifana F. Montanari F. Rosati O. Taccone S. Synlett 2004, 1832

<A NAME="RZ06307SS-8">8</A> Wilfred CD. Taylor RJK. Synlett 2004, 1628

<A NAME="RZ06307SS-9A">9a</A> Kim BH. Han R. Kim JS. Jun YM. Baik W. Lee BM. Heterocycles 2004, 63: 41

<A NAME="RZ06307SS-9B">9b</A> Yang DL. Fokas D. Li JZ. Yu LB. Baldino CM. Synthesis 2005, 47

<A NAME="RZ06307SS-10A">10a</A> Kokare ND. Nagawade RR. Rane VP. Shinde DB. Synthesis 2007, 766

<A NAME="RZ06307SS-10B">10b</A> Kotharkar SA. Jadhav MR. Nagawade RR. Bahekar SS. Shinde DB. Lett. Org. Chem. 2005, 2: 398

<A NAME="RZ06307SS-10C">10c</A> Nagawade RR. Khanna VV. Bhagwat SS. Shinde DB. Eur. J. Med. Chem. 2005, 40: 1325

<A NAME="RZ06307SS-10D">10d</A> Bahekar SS. Shinde DB. Tetrahedron Lett. 2004, 45: 7999

<A NAME="RZ06307SS-10E">10e</A> Bahekar SS. Kotharkar SA. Shinde DB. Mendeleev Commun. 2004, 210

<A NAME="RZ06307SS-11A">11a</A> Smith AB. Branca SJ. Guaciaro MA. Wovkulich PM. Korn A. Org. Synth. Coll. Vol. VII John Wiley & Sons; London: 1990. p.271

<A NAME="RZ06307SS-11B">11b</A> Meyers AI. Flanagan ME. Org. Synth. Coll. Vol. IX John Wiley & Sons; London: 1998. p.258

<A NAME="RZ06307SS-11C">11c</A> Politzer IR. Meyers AI. Org. Synth Coll. Vol. VI John Wiley & Sons; London: 1988. p.905

<A NAME="RZ06307SS-12">12</A> Fieser LF. Org. Coll. Vol. IV John Wiley & Sons; London: 1963. p.195

<A NAME="RZ06307SS-13">13</A> Apelian MR. Fung AS. Kennedy GJ. Degnan TF. J. Phys. Chem. 1996, 100: 16577

<A NAME="RZ06307SS-14A">14a</A> Varala R. Nasreen A. Enugala R. Adapa SR. Tetrahedron Lett. 2007, 48: 69

<A NAME="RZ06307SS-14B">14b</A> Peipei S. Zhixin H. J. Heterocycl. Chem. 2006, 43: 773

<A NAME="RZ06307SS-15A">15a</A> Lee JC. Laydon JT. McDonnell PC. Gallagher TF. Kumar S. Green D. McNulty D. Blumenthal N. Heys JR. Landvatter SW. Streckler JE. McLaugher MM. Siemens IR. Fisher SM. Livi JP. White JR. Adams JL. Young PR. Nature 1994, 372: 739

<A NAME="RZ06307SS-15B">15b</A> Maier T, Schmierer R, Bauer K, Bieringer H, Buerstell H, and Sachse B. inventors; US 4,820,335. 1989; Chem. Abstr. 1989, 111, 19494

<A NAME="RZ06307SS-15C">15c</A> Schierer R, Mildenberger H, and Buerstell H. inventors; DE 3614364. ; Chem. Abstr. 1988, 108, 37838

<A NAME="RZ06307SS-16A">16a</A> Wasserscheid P. Keim W. Angew Chem. Int. Ed. 2000, 39: 37872

<A NAME="RZ06307SS-16B">16b</A> Bourissou D. Guerret O. Ggabbai FT. Bertrand G. Chem. Rev. 2000, 100

<A NAME="RZ06307SS-17A">17a</A> Balalaie S. Arabanian A. Hashtroudi MS. Monatsh. Chem. 2000, 131: 945

<A NAME="RZ06307SS-17B">17b</A> Hayes JF. Mitchell MB. Wicks C. Heterocycles 1994, 38: 575

<A NAME="RZ06307SS-17C">17c</A> Lozinskaya NA. Tsybezova VV. Proskurnina MV. Zefirov NS. Russ. Chem. Bull. 2003, 52: 674

<A NAME="RZ06307SS-18A">18a</A> Weiss M. Abbel M. J. Am. Chem. Soc. 1948, 70: 3666

<A NAME="RZ06307SS-18B">18b</A> McKillop A. Swann B. Ford ME. Taylor EC. J. Am. Chem. Soc. 1973, 95: 3641

<A NAME="RZ06307SS-18C">18c</A> Zhang GS. Shi QZ. Chen MF. Cai K. Synth. Commun. 1997, 27: 953

<A NAME="RZ06307SS-19A">19a</A> Siddiqui SA. Palimkar SS. Daniel T. Lahoti RJ. Srinivason KV. Tetrahedron 2005, 61: 3539

<A NAME="RZ06307SS-19B">19b</A> Kidwai M. Mothsra P. Bansal V. Goyal R. Monatsh. Chem. 2006, 137: 1189

<A NAME="RZ06307SS-20">20</A> Subba Rao NV. Ratnam CV. Curr. Sci. 1955, 24: 9199

<A NAME="RZ06307SS-21">21</A> Puaschkina LN. Mazalov SA. Postovskii IY. Zh. Obsch. Khim. 1962, 32: 2624

<A NAME="RZ06307SS-22">22</A> Subba Rao NV. Ratnam CV. Proc. Indian Acad. Sci., Sect. A 1956, 43: 173

<A NAME="RZ06307SS-23">23</A> Perumal S. Mariappan S. Sevaraj S. ARKIVOC 2004, (viii): 46