Citation: Wang Kaixuan, Wang Lanzhi. Unexpected Rearrangement Reaction and Synthesis of Benzoxazoles[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1147-1152. doi: 10.6023/cjoc201809038 shu

Unexpected Rearrangement Reaction and Synthesis of Benzoxazoles

Wang Kaixuan ,
Wang Lanzhi ^,

College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang 050024

Corresponding author: Wang Lanzhi,
Received Date: 28 September 2018
Revised Date: 14 November 2018
Available Online: 9 April 2019
Fund Project: the National Natural Science Foundation of China 21276064Project supported by the National Natural Science Foundation of China (Nos.21776060, 21276064), and the Natural Science Foundation of Hebei Province (No.B2016205165)the National Natural Science Foundation of China 21776060the Natural Science Foundation of Hebei Province B2016205165

Figures(6)

Novel series of rearrangement reactions were herein reported that enable access to a variety of unique 2-aryl-3-(3'-oxobutenyl)-benzoxazole compounds 6a~6f from 2-aminophenol, aromatic aldehyde and 3-butyn-2-one as materials by nucleophilic conjugate addition, dehydration and rearrangement reactions and intramolecular cyclization in the presence of a catalytic amount of CH₃COOH in CH₂Cl₂ at ambient temperature. On the basis of products and intermediate products, a series of possible mechanism was presented and theoretically verified by density functional theory (DFT) method at B3LYP/6-31G (d, p) level from both molecular energy and atomic charge in Gaussian 03 package. The results show that the theory and experiment consistently explain the rationality of the reaction mechanism. The mechanism of rearrangement provides a basis for further study of this type of reaction. The advantage of this method is that a novel structure of benzoxazole derivative was synthesized successfully via a series of rearrangement reactions. Therefore, this method can be used as an attractive strategy for practical synthesis of nitrogen heterocyclic compounds.
- rearrangement reaction,
- benzoxazole,
- synthesis,
- reaction mechanism,
- density functional theory (DFT)
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