Microwave Assisted 1,3-Dipolar Cycloaddition Reaction of  exo-Glucal with Nitrone

Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (10): 1750-1755. Previous Articles Next Articles

Original Articles

微波促进的葡萄糖烯与硝酮的1,3-偶极环加成反应

李小六*; 王彦坡; 陈华 ; 李志伟; 邢春勇

(河北大学化学与环境科学学院化学生物学实验室保定 071002)

收稿日期:2008-02-02 修回日期:2008-03-24 发布日期:2008-10-20
通讯作者: 李小六

Microwave Assisted 1,3-Dipolar Cycloaddition Reaction of exo-Glucal with Nitrone

LI, Xiao-Liu* ; WANG, Yan-Po; CHEN, Hua; LI, Zhi-Wei; XING, Chun-Yong

(Laboratory of Chemical Biology, College of Chemistry and Environmental Sciences, Hebei University, Baoding 071002)

Received:2008-02-02 Revised:2008-03-24 Published:2008-10-20
Contact: LI, Xiao-Liu

Abstract

With microwave irradiation, the efficiency of the 1,3-dipolar cycloaddition of exo-glucal (1) with nitrones 2 was remarkably improved, and the yield of the microwave assisted reaction in a seamless pressure vial at 200 ℃ for 2 min could be up to 96%, providing a practical and convenient method for preparing spiro-isoxazolidine glycosides which are very important intermediates for synthesizing various C-glycosides possessing functional groups.

Key words: 1,3-dipolar cycloaddition, microwave assisted, exo-glycal, spiro-isoxazolidine glycoside, nitrone

Cite this article

LI, Xiao-Liu* ; WANG, Yan-Po; CHEN, Hua; LI, Zhi-Wei; XING, Chun-Yong. Microwave Assisted 1,3-Dipolar Cycloaddition Reaction of exo-Glucal with Nitrone[J]. Chin. J. Org. Chem., 2008, 28(10): 1750-1755.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Ning Zou, Xiaoting Qin, Zhixin Wang, Weimin Shi, Dongliang Mo. Advances on the Synthesis and Application of α,β-Unsaturated Nitrones [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4535-4553.
[2]	Yue Guizhou, Liu Bo. Research Progress on [3+n] (n≥3) Cycloaddition of 1,3-Diploes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3132-3153.
[3]	Li Minglong, Cao Xixian, You Jun, Yu Yanchao, Wu Wenju, Liu Bo. Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acyl Compounds Catalyzed by Chiral Bisoxazoline Metal Complex [J]. Chin. J. Org. Chem., 2019, 39(6): 1642-1649.
[4]	Li Qianmei, Pang Kaisheng, Zhao Jianping, Liu Xinghai, Weng Jianquan. Synthesis and Biological Activity of Novel 1,3,4-Thiadiazole Thioether Derivatives Containing Pyrimidine Moiety [J]. Chin. J. Org. Chem., 2017, 37(4): 1009-1015.
[5]	Liu Xunshen, Li Meimei, You Jun, Liu Bo. Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acylpyrazoles Catalyzed by Ni-DBFOX/Ph [J]. Chin. J. Org. Chem., 2017, 37(1): 86-91.
[6]	Li Xiaoliu, Wang Wei, Li Rui, Zhang Pingzhu, Chen Hua. Efficient and Stereoselective Synthesis of Carbohydrate α,β-Un- saturated Esters by Microwave Assisted Wittig Reaction [J]. Chin. J. Org. Chem., 2012, 32(08): 1519-1525.
[7]	Lan Cong, Xu Pan, Liang Ronghui, Xu Zelong, Xia Zhining. Study on the Microwave Effect in the Claisen Rearrangement of the Allyl Phenyl Ethers [J]. Chin. J. Org. Chem., 2012, 32(04): 765-769.
[8]	LI Yan^1,2,WANG Yu-Lu*^,1. Progress in the Synthesis of 2-Substituent-Benzothiazoles [J]. Chin. J. Org. Chem., 2006, 26(06): 878-884.
[9]	HU Xiao-Fen,FENG Ya-Qing^*,LI Xiao-Fang. Chiral Lewis Acid-Catalyzed 1,3-Dipolar Cycloadditions between [J]. Chin. J. Org. Chem., 2005, 25(01): 1-7.
[10]	CHEN QINGHUA;XIE MENGXIA;JIA XIBEI;WANG XUELIANG. Studies on intramolecular 1,3-dipolar cycloaddition reactions IV: The thermochemical and photochemical reactions of some 1,3-dipolar nitrone systems and related regioselectivities [J]. Chin. J. Org. Chem., 1989, 9(2): 156-162.

微波促进的葡萄糖烯与硝酮的1,3-偶极环加成反应

Microwave Assisted 1,3-Dipolar Cycloaddition Reaction of exo-Glucal with Nitrone

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 10

Recommended Articles

Metrics

Comments