Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans

被引：3

作者：

Sun, Manman ^{[1
,2
]}

Song, Jinyu ^{[1
,2
]}

Wang, Lei ^{[3
]}

Yin, Wenguang ^{[3
]}

Miao, Maozhong ^{[3
]}

Ren, Hongjun ^{[1
,2
]}

机构：

[1] Taizhou Univ, Adv Res Inst, 1139 Shifu Ave, Taizhou 318000, Peoples R China

[2] Taizhou Univ, Dept Chem, 1139 Shifu Ave, Taizhou 318000, Peoples R China

[3] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Peoples R China

来源：

SYNLETT | 2020年 / 31卷 / 08期

关键词：

propargylation; ortho-quinone methides; alkynyl zinc reagents; benzofurans; TERMINAL ALKYNES; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; CATALYZED 1,4-ADDITION; ALLYLIC ALKYLATION; NUCLEOPHILES; CYCLIZATION; ANNULATION; INDOLES; SYSTEM;

D O I：

10.1055/s-0039-1691739

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition-metal-free propargylation of ortho-quinone methides (o-QMs) with alkynyl zinc reagents was achieved. A conjugate alkynylation of an o-QM and subsequent cyclization sequence in the presence of KOt-Bu for the synthesis of 2,3-disubstituted benzofurans in one pot was developed. This efficient strategy exhibits good functional-group compatibility and gives moderate to good yields. The present reaction might serve as an attractive method for the synthesis of polysubstituted benzofurans.

引用

页码：818 / 822

页数：5

共 60 条

[51] ASYMMETRIC CONJUGATE ADDITION [J].

ROSSITER, BE ;

SWINGLE, NM .

CHEMICAL REVIEWS, 1992, 92 (05) :771-806

[52] Phenolic constituents from Dalbergia cochinchinensis [J].

Shirota, O ;

Pathak, V ;

Sekita, S ;

Satake, M ;

Nagashima, Y ;

Hirayama, Y ;

Hakamata, Y ;

Hayashi, T .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (08) :1128-1131

[53] ortho-Quinone methide (o-QM): a highly reactive, ephemeral and versatile intermediate in organic synthesis [J].

Singh, Maya Shankar ;

Nagaraju, Anugula ;

Anand, Namrata ;

Chowdhury, Sushobhan .

RSC ADVANCES, 2014, 4 (99) :55924-55959

[54] The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups [J].

Trost, Barry M. ;

Weiss, Andrew H. .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (7-8) :963-983

[55] Synthesis and structure-affinity-activity relationships of novel benzofuran derivatives as MT2 melatonin receptor selective ligands [J].

Wallez, V ;

Durieux-Poissonnier, S ;

Chavatte, P ;

Boutin, JA ;

Audinot, V ;

Nicolas, JP ;

Bennejean, C ;

Delagrange, P ;

Renard, P ;

Lesieur, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (13) :2788-2800

[56] ortho-Quinone Methides in Natural Product Synthesis [J].

Willis, Nicky J. ;

Bray, Christopher D. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (30) :9160-9173

[57] Enantioselective synthesis of functionalized 2-amino-4H-chromenes via the o-quinone methides generated from 2-(1-tosylalkyl)phenols [J].

Wu, Bo ;

Gao, Xiang ;

Yan, Zhong ;

Huang, Wen-Xue ;

Zhou, Yong-Gui .

TETRAHEDRON LETTERS, 2015, 56 (29) :4334-4338

[58] Iron-Catalyzed Regioselective Hydroaryloxylation of CC Triple Bonds: An Efficient Synthesis of 2H-1-Benzopyran Derivatives [J].

Xu, Xiaobing ;

Liu, Jun ;

Liang, Linfeng ;

Li, Hongfeng ;

Li, Yanzhong .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) :2599-2604

[59] Copper-Catalyzed Dehydrative Cyclization of 1-(2-Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2-Phosphorylmethylbenzofurans [J].

Zhang, Ming ;

Yang, Jianlin ;

Xu, Qing ;

Dong, Chao ;

Han, Li-Biao ;

Shen, Ruwei .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (02) :334-345

[60] Palladium-catalyzed 1,4-addition of terminal alkynes to unsaturated carbonyl compounds promoted by electron-rich ligands [J].

Zhou, Lei ;

Chen, Liang ;

Skouta, Rachid ;

Jiang, Huan-Feng ;

Li, Chao-Jun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (16) :2969-2977

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