A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations

Xiaobing Yang; Fangzhong Hu; Hongjing Di; Xinxin Cheng; Dan Li; Xiaoli Kan; Xiaomao Zou; Qichun Zhang

doi:10.1039/c4ob01300j

Author(s)

Xiaobing Yang
Fangzhong Hu
Hongjing Di
Xinxin Cheng
Dan Li
Xiaoli Kan
Xiaomao Zou

Detail(s)

Original language	English
Pages (from-to)	8947-8951
Journal / Publication	Organic and Biomolecular Chemistry
Volume	12
Issue number	44
Online published	9 Sept 2014
Publication status	Published - 28 Nov 2014
Externally published	Yes

Link(s)

DOI	DOI https://doi.org/10.1039/c4ob01300j Final Published version
	Check@CityULib
Link to Scopus	https://www.scopus.com/record/display.uri?eid=2-s2.0-84908391552&origin=recordpage
Permanent Link	https://scholars.cityu.edu.hk/en/publications/publication(6994410e-2aaf-4609-a419-33e38374965b).html

Abstract

A convenient base-mediated strategy to synthesize 3-aryol-4-methyl (or benzyl)-2-methylthio furans 2 (trisubstituted furans) has been developed through the domino coupling/annulations between available α-oxo ketene dithioacetals 1 and propargyl alcohols. In this strategy, these types of bases play an important role in driving the domino coupling reaction of propargyl alcohols and further intramolecular annulations to realize the target compounds. The possible mechanism for the formation of the various products is believed to involve the generation of allenes 7, followed by intramolecular annulations.

Citation Format(s)

[ RIS ] [ BibTeX ]

A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations. / Yang, Xiaobing; Hu, Fangzhong; Di, Hongjing et al.
In: Organic and Biomolecular Chemistry, Vol. 12, No. 44, 28.11.2014, p. 8947-8951.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

Yang, X, Hu, F, Di, H, Cheng, X, Li, D, Kan, X, Zou, X & Zhang, Q 2014, 'A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations', Organic and Biomolecular Chemistry, vol. 12, no. 44, pp. 8947-8951. https://doi.org/10.1039/c4ob01300j

Yang, X., Hu, F., Di, H., Cheng, X., Li, D., Kan, X., Zou, X., & Zhang, Q. (2014). A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations. Organic and Biomolecular Chemistry, 12(44), 8947-8951. https://doi.org/10.1039/c4ob01300j

Yang X, Hu F, Di H, Cheng X, Li D, Kan X et al. A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations. Organic and Biomolecular Chemistry. 2014 Nov 28;12(44):8947-8951. Epub 2014 Sept 9. doi: 10.1039/c4ob01300j

Yang, Xiaobing ; Hu, Fangzhong ; Di, Hongjing et al. / A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations. In: Organic and Biomolecular Chemistry. 2014 ; Vol. 12, No. 44. pp. 8947-8951.