Citation: Zhan Zhu LIU, Ye Feng TANG, Shi Zhi CHEN. Formation of Benzyl Oxazole, A Competitive Path with the Classical Bishler-Napieralski Reaction[J]. Chinese Chemical Letters, ;2001, 12(11): 947-950. shu

Formation of Benzyl Oxazole, A Competitive Path with the Classical Bishler-Napieralski Reaction

Institute of Materia Medica, Chinese Academy of Material Sciences & Peking Union Medical College, Beijing 100050

Received Date: 4 April 2001

Several aromatic ring-substituted N-acetyl-phenylalanine methyl esters were treated with POCl₃ in refluxing benzene, which is the typical condition of B-N reaction. It was found that the normal B-N product 3, 4-dihydroisoquinoline-3-carboxylic acid methyl ester and/or 5-benzyl-2-methyl-4-methoxy oxazole could be obtained. The result depended mainly upon the electron-donating property of the substitutes on the benzene ring. Strong electron-donating groups located at para-or ortho-to the cyclization site will facilitate the formation of the normal B-N product 2. On the other hand, the absence or weak electron-donating groups tended to yield the oxazole product 3. It was established that the formation ofbenzyl oxazole is the competitive path with the B-N reaction. In this article, an explanation was given based on the mechanism of Bishler-Napieralski reaction.
- Bishler-Napieralski reaction,
- benzyl oxazole,
- 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid,
- N-acetyl-phenylalanine methyl ester
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