引用本文:
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.
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.
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.
Formation of Benzyl Oxazole, A Competitive Path with the Classical Bishler-Napieralski Reaction
摘要:
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.
English
Formation of Benzyl Oxazole, A Competitive Path with the Classical Bishler-Napieralski Reaction
Abstract:
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.
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