One-pot synthesis of benzofused 8-oxabicyclo[3.3.1]nonanes via GaCl3-mediated cyclocondensation of o-allylbenzaldehydes and 1,3-dicarbonyl synthons

Meng-Yang Chang; Yan-Ling Lee

doi:10.1039/D4OB00016A

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One-pot synthesis of benzofused 8-oxabicyclo[3.3.1]nonanes via GaCl₃-mediated cyclocondensation of o-allylbenzaldehydes and 1,3-dicarbonyl synthons†

Meng-Yang Chang

*^abc and Yan-Ling Lee^a

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* Corresponding authors

^a Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
E-mail: mychang@kmu.edu.tw

^b Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan

^c NPUST College of Professional Studies, National Pingtung University of Science and Technology, Pingtung 912, Taiwan

Abstract

GaCl₃-mediated one-pot cyclocondensation of o-allylbenzaldehydes and 1,3-dicarbonyls generates benzofused 8-oxabicyclo[3.3.1]nonanes in moderate to good yields in refluxing MeNO₂ under easy-operational conditions. A plausible mechanism is proposed and discussed here. In the overall reaction process, various metal chloride-promoted conditions were investigated for one-pot cyclocondensation.

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Article information

DOI: https://doi.org/10.1039/D4OB00016A
Article type: Paper
Submitted: 05 Jan 2024
Accepted: 27 Jan 2024
First published: 29 Jan 2024

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Org. Biomol. Chem., 2024,22, 1646-1653

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One-pot synthesis of benzofused 8-oxabicyclo[3.3.1]nonanes via GaCl₃-mediated cyclocondensation of o-allylbenzaldehydes and 1,3-dicarbonyl synthons

M. Chang and Y. Lee, Org. Biomol. Chem., 2024, 22, 1646 DOI: 10.1039/D4OB00016A

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Organic & Biomolecular Chemistry