Approach to 2'-(Dialkylamino)-1-alkyl-4'H-spiro[indoline-3,5'-oxazole]-2,4'-diones and 1,3-Oxazin-4-ones via Cyclization of Vilsmeier Salts with α-Hydroxy and β-Carbonyl Amides

doi:10.1007/s40242-019-8307-2

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (2): 216-220.doi: 10.1007/s40242-019-8307-2

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Approach to 2'-(Dialkylamino)-1-alkyl-4'H-spiro[indoline-3,5'-oxazole]-2,4'-diones and 1,3-Oxazin-4-ones via Cyclization of Vilsmeier Salts with α-Hydroxy and β-Carbonyl Amides

DAI Jianan, LIU Bengen, WEI Zhonglin, CAO Jungang, LIANG Dapeng, DUAN Haifeng, LIN Yingjie

Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012, P. R. China

Received:2018-09-25 Revised:2018-11-20 Online:2019-04-01 Published:2019-04-30
Contact: LIN Yingjie, DUAN Haifeng E-mail:linyj@jlu.edu.cn;duanhf@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.51373067).

Abstract

Abstract: A straightforward and efficient synthetic method of 2'-(dialkylamino)-1-alkyl-4'H-spiro[indoline-3,5'-oxazole]-2,4'-diones and 2-(dialkylamino)-5,6-dihydro-4H-naphtho[2,1-e] [1,3]oxazin-4-one derivatives have been developed from α-hydroxy and β-carbonyl amides and various Vilsmeier salts. A wide range of heterocyclic compounds were obtained in excellent yields(up to 97%), which will provide promising candidates for chemical biology and drug discovery.

Key words: Spirooxindole unit, 2-Oxazolin-4-ones core structure, 3-Oxazin-4-ones core structure

DAI Jianan, LIU Bengen, WEI Zhonglin, CAO Jungang, LIANG Dapeng, DUAN Haifeng, LIN Yingjie. Approach to 2'-(Dialkylamino)-1-alkyl-4'H-spiro[indoline-3,5'-oxazole]-2,4'-diones and 1,3-Oxazin-4-ones via Cyclization of Vilsmeier Salts with α-Hydroxy and β-Carbonyl Amides[J]. Chemical Research in Chinese Universities, 2019, 35(2): 216-220.

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Approach to 2'-(Dialkylamino)-1-alkyl-4'H-spiro[indoline-3,5'-oxazole]-2,4'-diones and 1,3-Oxazin-4-ones via Cyclization of Vilsmeier Salts with α-Hydroxy and β-Carbonyl Amides

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