咪唑和酰氯反应环裂解为烯二胺酰胺中间体，接着加热得到2-取代咪唑的反应。

反应机理

反应操作

Imidazole (3). Im 1 (9.2 g, 54 mmol) in EA (140 mL) was treated with benzoyl chloride (15.7 g, 112 mmol) in EA (40 mL) and 1M NaHCO3 (380 mL) was added simultaneously in 1 h, then a portion of benzoyl chloride (15.7 g, 112 mmol) in EA and 1M NaHCO3 (280 mL) were added followed by another portion of 1M NaHCO3 (200 mL). After 24 h, the organic layer was concentrated and the residue dissolved in THF (300 mL). The THF solution was stirred with 10% NaHCO3 (600 mL) for 24 h to decompose any N-formyl intermediate and to remove benzoic acid. Extraction with EA, drying (Na2SO4), solvent evaporation and recrystallization from EA:hexane afforded 16.24 g of 3 in 84% yield, mp 128–129 C.

【Altman J, J Chem Soc Perkin, 1984, 1, 59】

相关文献

1 Bamberger E Liebigs Ann 1893 273 342

2 Babad E J Heterocycl Chem 1969 6 235

3 Kimoto H J Org Chem 1978 43 3403

4 Grace ME J Am Chem Soc 1980 102 6784

5 Altman J J Chem Soc Perkin 1984 1 59

6 Altman J J Chem Soc Chem Commun 1985 1133

7 Yadan JC J Org Chem 1995 60 6296

8 Itaya T Chem Pharm Bull 1997 45 75

9 Zhang L Biorg Med Chem Lett 1999 9 1751

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 27.