Summary.
Elemental iodine is used as an efficient catalyst for the synthesis of 2,4,5-triarylimidazoles in excellent yields via condensation of benzoin, ammonium acetate, and aromatic aldehydes. This is a simple, one-pot, high yielding technique using cheap, non-toxic iodine in catalytic amounts.
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JC Lee JT Laydon PC McDonnell TF Gallagher S Kumar D Green D McNulty N Blumenthal JR Heys SW Landvatter JE Strickler MM McLaughlin IR Siemens SM Fisher JP Livi JR White JL Adams PR Young (1994) Nature 372 739 Occurrence Handle1:CAS:528:DyaK2MXisl2qu70%3D Occurrence Handle10.1038/372739a0
Maier T, Schmierer R, Bauer K, Bieringer H, Buerstell H, Sachse B, US Patent (1989) 4820335; (1989) Chem Abstr 111: 19494
Schmierer R, Mildenberger H, Buerstell H, German Patent (1987) 361464; (1988) Chem Abstr 108: 37838
J Heeres LJJ Backx JH Mostmans J Vancustem (1979) J Med Chem 22 1003 Occurrence Handle1:CAS:528:DyaE1MXks1ymsrc%3D Occurrence Handle10.1021/jm00194a023
P Wasserscheid W Keim (2000) Angew Chem Int Ed Eng 39 3772 Occurrence Handle1:CAS:528:DC%2BD3cXotFyqtLk%3D Occurrence Handle10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
D Bourissou O Guerret FP Gabbai G Bertrand (2000) Chem Rev 100 39 Occurrence Handle1:CAS:528:DyaK1MXotVemu7w%3D Occurrence Handle10.1021/cr940472u
a) Davidson D, Weiss M, Jelling M (1937) J Org Chem 2: 319; b) Cook AH, Jones DC (1941) J Chem Soc 278; c) White DM, Sonnenberg J (1964) J Org Chem 23: 1926; d) Japp FR, Robinson MM (1882) Chem Ber 15: 1269; e) Clark NG, Lawkill E (1975) Tetrahedron Lett 2717; f) Zhng C, Moran EJ, Woiwode TF, Shart KM, Mjalli AMM (1996) Tetrahedron Lett 37: 751; g) Frantz DE, Morency L, Sohili A, Murry JA, Grabowski EJJ, Tillyer R (2004) Org Lett 6: 843; h) Siddiqui SA, Narkhede VC, Palimkar SS, Daniel T, Lahoti RJ, Srinivasan KV (2005) Tetrahedron 61: 3539
a) Balalaie S, Arabanian A (2000) Green Chem 2: 274; b) Usyatinsky AY, Khmelnitsky YL (2000) Tetrahedron Lett 41: 5031; c) Cobb JM, Grimster N, Khan N, Lai JYQ, Payne MJ, Payne LJ, Raynham T, Taylor J (2000) Tetrahedron Lett 43: 7557; d) Xu L, Wan Li-F, Salchi H, Deng W, Guo Q-X (2004) Heterocycles 63: 1613; e) Wolkenberg SE, Wisnoski DD, Leister WM, Wang Y, Zhao Z, Lindsley CW (2004) Org Lett 6: 1453; f) Zhou JF, Song Y-Z, Yang Y-L, Zhu Y-L, Tu S-J (2005) Synth Commun 35: 1369
Shun-Yi Wang (2004) Syn Lett 14 2642
a) Kidwai M, Mishra P, Dave B, Bhushan KR, Saxena RK, Singh M (2000) Monatsh Chem 131: 1207; b) Kidwai M, Saxena S, Mohan R, Venkatramanan R (2002) J Chem Soc, Perkin Trans 1 1845; c) Kidwai M, Mothsra P, Mohan R, Biswas S (2005) Bioorg Med Chem Lett 15: 915
a) Weiss M, Abbel M (1948) J Am Chem Soc 70: 3666; b) McKillop A, Swann B, Ford ME, Taylor EC (1973) J Am Chem Soc 95: 3641; c) Zhang GS, Shi QZ, Chen MF, Cai K (1997) Syn Commun 27: 953
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Kidwai, M., Mothsra, P., Bansal, V. et al. Efficient Elemental Iodine Catalyzed One-Pot Synthesis of 2,4,5-Triarylimidazoles. Monatsh. Chem. 137, 1189–1194 (2006). https://doi.org/10.1007/s00706-006-0518-9
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DOI: https://doi.org/10.1007/s00706-006-0518-9