Feeding sequence-regulated divergent (4 + 1 + 1′) annulations of α-bromo carbonyls and 1-azadienes <i>via</i> computational calculation-based mechanism elucidation

Ouyang, Qin; Zeng, Rong; Zheng, Wei; Peng, Rui-Kun; Yan, Peng; Yang, Jie; Zhou, Qian; Gu, Jing; Zheng, Pengfei; Chen, Ying‐Chun

doi:10.1039/d2qo00052k

Org. Chem. Front.

2022

DOI: 10.1039/d2qo00052k

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Feeding sequence-regulated divergent (4 + 1 + 1′) annulations of α-bromo carbonyls and 1-azadienes via computational calculation-based mechanism elucidation

Qin Ouyang

Rong Zeng

Wei Zheng

et al.

Abstract: By investigating the mechanism of our previously reported (4 + 1 + 1) annulations of α-bromo carbonyls and 1-azadienes via density functional theory (DFT) calculations, the formation of a carbon...

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Additive‐Controlled Divergent [4+2] Cycloaddition and 1,4‐Michael Addition Reaction of Benzofuran‐Derived Azadienes with Enamides: Access to Decahydrobenzofuro[3,2‐b]quinolines

Tian,

Shi,

Gao

et al. 2024

ChemistrySelect

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We describe herein the additive‐controlled divergent [4+2] cycloaddition and 1,4‐Michael addition reaction of benzofuran‐derived azadienes (BDAs) with enamides. An unprecedented [4+2] cycloaddition reaction of BDAs and enamide compounds was developed in the presence of 4 Å MS, providing a variety of structurally complex decahydrobenzofuro[3,2‐b]quinolines (13 examples) in moderate to excellent yields (59–98 % yields) with single diastereoisomer obtained. While employing MgSO4 as desiccant, the chemoselectivity was switched to the 1,4‐addition reactions, leading to a wide range of highly functionalized hybrids of benzofurans and enamide compounds (25 examples) in 25–94 % yields under mild conditions.

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Additive‐Controlled Divergent [4+2] Cycloaddition and 1,4‐Michael Addition Reaction of Benzofuran‐Derived Azadienes with Enamides: Access to Decahydrobenzofuro[3,2‐b]quinolines

Tian,

Shi,

Gao

et al. 2024

ChemistrySelect

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Ethylene carbonate generated efficiently via ethylene oxide and CO2 on the Li-MgO(1 0 0) surface based on the synergistic activation of bimetals without halogen

Guo

Zhang

Sun

et al. 2023

Fuel

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Feeding sequence-regulated divergent (4 + 1 + 1′) annulations of α-bromo carbonyls and 1-azadienes via computational calculation-based mechanism elucidation

Abstract: By investigating the mechanism of our previously reported (4 + 1 + 1) annulations of α-bromo carbonyls and 1-azadienes via density functional theory (DFT) calculations, the formation of a carbon...

Cited by 2 publications

References 39 publications

Additive‐Controlled Divergent [4+2] Cycloaddition and 1,4‐Michael Addition Reaction of Benzofuran‐Derived Azadienes with Enamides: Access to Decahydrobenzofuro[3,2‐b]quinolines

Additive‐Controlled Divergent [4+2] Cycloaddition and 1,4‐Michael Addition Reaction of Benzofuran‐Derived Azadienes with Enamides: Access to Decahydrobenzofuro[3,2‐b]quinolines

Ethylene carbonate generated efficiently via ethylene oxide and CO2 on the Li-MgO(1 0 0) surface based on the synergistic activation of bimetals without halogen

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