Syntheses of 2-Benzylbenzofuran Derivatives and 2-Aryl-nitrochroman Derivatives from Nitroalkene Precursors

Chia Yu Huang; Chun Wei Kuo; Veerababurao Kavala; Ching Fa Yao

doi:10.1002/ejoc.201600314

Syntheses of 2-Benzylbenzofuran Derivatives and 2-Aryl-nitrochroman Derivatives from Nitroalkene Precursors

Chia Yu Huang^*, Chun Wei Kuo, Veerababurao Kavala, Ching Fa Yao

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

Simple and straightforward methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described. Benzofurans were generated from nitroalkenes by reduction with NaBH₄ followed by a Nef reaction and acid-mediated cyclization, whereas 3-substituted 2-benzylbenzofurans were prepared from nitroalkenes by reactions with Grignard reagents followed by a Nef reaction and an acid-mediated cyclization in a one-pot process. The synthesis of chromans involved a Knoevenagel condensation and the 1,4-diazabicyclo[2.2.2]octane (DABCO) assisted cyclization of β-(2-hydroxyphenyl)-nitroethanes and benzaldehydes, also in a one-pot process. Simple and convenient methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described.

Original language	English
Pages (from-to)	2720-2734
Number of pages	15
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	15
DOIs	https://doi.org/10.1002/ejoc.201600314
Publication status	Published - 2016 May 1

Keywords

Cyclization
Nef reaction
Nitroalkenes
Oxygen heterocycles
Synthesis design

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201600314

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title = "Syntheses of 2-Benzylbenzofuran Derivatives and 2-Aryl-nitrochroman Derivatives from Nitroalkene Precursors",

abstract = "Simple and straightforward methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described. Benzofurans were generated from nitroalkenes by reduction with NaBH4 followed by a Nef reaction and acid-mediated cyclization, whereas 3-substituted 2-benzylbenzofurans were prepared from nitroalkenes by reactions with Grignard reagents followed by a Nef reaction and an acid-mediated cyclization in a one-pot process. The synthesis of chromans involved a Knoevenagel condensation and the 1,4-diazabicyclo[2.2.2]octane (DABCO) assisted cyclization of β-(2-hydroxyphenyl)-nitroethanes and benzaldehydes, also in a one-pot process. Simple and convenient methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described.",

keywords = "Cyclization, Nef reaction, Nitroalkenes, Oxygen heterocycles, Synthesis design",

author = "Huang, {Chia Yu} and Kuo, {Chun Wei} and Veerababurao Kavala and Yao, {Ching Fa}",

note = "Publisher Copyright: Copyright {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

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doi = "10.1002/ejoc.201600314",

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AU - Huang, Chia Yu

AU - Kuo, Chun Wei

AU - Kavala, Veerababurao

AU - Yao, Ching Fa

PY - 2016/5/1

Y1 - 2016/5/1

N2 - Simple and straightforward methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described. Benzofurans were generated from nitroalkenes by reduction with NaBH4 followed by a Nef reaction and acid-mediated cyclization, whereas 3-substituted 2-benzylbenzofurans were prepared from nitroalkenes by reactions with Grignard reagents followed by a Nef reaction and an acid-mediated cyclization in a one-pot process. The synthesis of chromans involved a Knoevenagel condensation and the 1,4-diazabicyclo[2.2.2]octane (DABCO) assisted cyclization of β-(2-hydroxyphenyl)-nitroethanes and benzaldehydes, also in a one-pot process. Simple and convenient methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described.

AB - Simple and straightforward methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described. Benzofurans were generated from nitroalkenes by reduction with NaBH4 followed by a Nef reaction and acid-mediated cyclization, whereas 3-substituted 2-benzylbenzofurans were prepared from nitroalkenes by reactions with Grignard reagents followed by a Nef reaction and an acid-mediated cyclization in a one-pot process. The synthesis of chromans involved a Knoevenagel condensation and the 1,4-diazabicyclo[2.2.2]octane (DABCO) assisted cyclization of β-(2-hydroxyphenyl)-nitroethanes and benzaldehydes, also in a one-pot process. Simple and convenient methods for the synthesis of 2-benzylbenzofuran, 3-substituted 2-benzylbenzofuran, and 2-aryl-nitrochroman derivatives are described.

KW - Cyclization

KW - Nef reaction

KW - Nitroalkenes

KW - Oxygen heterocycles

KW - Synthesis design

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Syntheses of 2-Benzylbenzofuran Derivatives and 2-Aryl-nitrochroman Derivatives from Nitroalkene Precursors

Abstract

Keywords

ASJC Scopus subject areas

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