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

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^*

^*Corresponding author for this work

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

16 Citations (Scopus)

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.

Original language	English
Pages (from-to)	8947-8951
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	44
Online published	9 Sept 2014
DOIs	https://doi.org/10.1039/c4ob01300j
Publication status	Published - 28 Nov 2014
Externally published	Yes

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@article{6994410e2aaf4609a41933e38374965b,

title = "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",

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. ",

author = "Xiaobing Yang and Fangzhong Hu and Hongjing Di and Xinxin Cheng and Dan Li and Xiaoli Kan and Xiaomao Zou and Qichun Zhang",

year = "2014",

month = nov,

day = "28",

doi = "10.1039/c4ob01300j",

language = "English",

volume = "12",

pages = "8947--8951",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "44",

}

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

TY - JOUR

T1 - 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

AU - Yang, Xiaobing

AU - Hu, Fangzhong

AU - Di, Hongjing

AU - Cheng, Xinxin

AU - Li, Dan

AU - Kan, Xiaoli

AU - Zou, Xiaomao

AU - Zhang, Qichun

PY - 2014/11/28

Y1 - 2014/11/28

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84908391552

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-84908391552&origin=recordpage

U2 - 10.1039/c4ob01300j

DO - 10.1039/c4ob01300j

M3 - RGC 21 - Publication in refereed journal

SN - 1477-0520

VL - 12

SP - 8947

EP - 8951

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 44

ER -

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

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