Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones

Feng Lian Zhang; Yi Feng Wang; Shunsuke Chiba

doi:10.1039/c3ob41393d

Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones

Feng Lian Zhang, Yi Feng Wang, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

Abstract

Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K₃PO₄ in DMF at 60°C under an O ₂ atmosphere via benzylic C-H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes with Cs₂CO₃ in DMSO at 100°C could result in oxidative skeletal rearrangement to deliver quinazolinones as a major product. This orthogonal product selectivity could be realized by difference of the reaction temperature as well as selection of the solvents and inorganic bases.

Original language	English
Pages (from-to)	6003-6007
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	36
DOIs	https://doi.org/10.1039/c3ob41393d
Publication status	Published - Sept 28 2013
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60°C under an O 2 atmosphere via benzylic C-H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes with Cs2CO3 in DMSO at 100°C could result in oxidative skeletal rearrangement to deliver quinazolinones as a major product. This orthogonal product selectivity could be realized by difference of the reaction temperature as well as selection of the solvents and inorganic bases.",

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PY - 2013/9/28

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N2 - Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60°C under an O 2 atmosphere via benzylic C-H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes with Cs2CO3 in DMSO at 100°C could result in oxidative skeletal rearrangement to deliver quinazolinones as a major product. This orthogonal product selectivity could be realized by difference of the reaction temperature as well as selection of the solvents and inorganic bases.

AB - Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60°C under an O 2 atmosphere via benzylic C-H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes with Cs2CO3 in DMSO at 100°C could result in oxidative skeletal rearrangement to deliver quinazolinones as a major product. This orthogonal product selectivity could be realized by difference of the reaction temperature as well as selection of the solvents and inorganic bases.

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Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones

Abstract

ASJC Scopus Subject Areas

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