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. 2019 Apr 25;9(22):12567-12571.
doi: 10.1039/c9ra02144b. eCollection 2019 Apr 17.

Synthesis of poly-functionalized benzofurans via one-pot domino oxidation/[3+2] cyclization reactions of a hydroquinone ester and ynamides

Dongxin Zhang  1 , Jingjing Man  1 , Yan Chen  1 , Lei Yin  1 , Junchao Zhong  1 , Qian-Feng Zhang  1
Affiliations

Synthesis of poly-functionalized benzofurans via one-pot domino oxidation/[3+2] cyclization reactions of a hydroquinone ester and ynamides

Dongxin Zhang et al. RSC Adv. .

Abstract

Densely substituted amino-functionalized benzofurans were concisely accessed via the first one-pot domino oxidation/[3+2] cyclization of a hydroquinone ester and easily accessible ynamides under mild conditions in a short time. The complex benzofurans were able to be efficiently synthesized all from simple and inexpensive starting materials in two steps.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Direct accesses to benzofuran derivatives under oxidative conditions.
Scheme 2
Scheme 2. Substrate scope of the one-pot domino oxidation/[3+2] cyclization reaction. Reaction conditions: hydroquinone ester 5 (0.12 mmol), Ag2O (0.24 mmol), and MgSO4 (0.24 mmol) were mixed in CH2Cl2 (2.0 mL) and the mixture was stirred for 2 h, and then 1 (0.10 mmol) and Sc(OTf)3 (0.002 mmol) were added.
Scheme 3
Scheme 3. (a) Concise access to complex benzofurans from simple and inexpensive starting materials. (b) A large scale reaction for the synthesis of 3h.
Scheme 4
Scheme 4. Proposed mechanism for the one-pot domino oxidation/[3+2] cyclization.
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