Iodine-Mediated, Microwave-Assisted Synthesis of 1-Arylnaphthofurans via Cyclization of 1-(1′-Arylvinyl)-2-naphthols

V. Kameshwara Rao; Pinku Kaswan; Ganesh M. Shelke; Ashley Ryan; Mukund Jha; Anil Kumar

doi:10.1055/s-0035-1560268

Synthesis, Table of Contents

Synthesis 2015; 47(24): 3990-3996
DOI: 10.1055/s-0035-1560268

paper

Iodine-Mediated, Microwave-Assisted Synthesis of 1-Arylnaphthofurans via Cyclization of 1-(1′-Arylvinyl)-2-naphthols

Authors

V. Kameshwara Rao

^aDepartment of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India Email: anilkumar@pilani.bits-pilani.ac.in
Pinku Kaswan

^aDepartment of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India Email: anilkumar@pilani.bits-pilani.ac.in
Ganesh M. Shelke

^aDepartment of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India Email: anilkumar@pilani.bits-pilani.ac.in

^bDepartment of Biology and Chemistry, Nipissing University, North Bay, ON, P1B 8L7, Canada
Ashley Ryan

^bDepartment of Biology and Chemistry, Nipissing University, North Bay, ON, P1B 8L7, Canada
Mukund Jha

^bDepartment of Biology and Chemistry, Nipissing University, North Bay, ON, P1B 8L7, Canada
Anil Kumar*

^aDepartment of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India Email: anilkumar@pilani.bits-pilani.ac.in

Abstract

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Abstract

A metal-free, one-pot, iodine-mediated, microwave-assisted cyclization of 1-(1′-arylvinyl)-2-naphthols (ortho-vinylnaphthols) into 1-arylnaphthofurans is developed. The 1-arylnaphthofurans are isolated in good to excellent yields (65–90%) using two equivalents of iodine in acetonitrile. The reactions proceed via the formation of 1-(2-iodo-1-phenylvinyl)naphthalen-2-ols as intermediates. Overall, the protocol is convenient as the reactions occur smoothly without the requirement of a transition-metal catalyst.

Key words

iodine-mediated - microwave-assisted - hydroarylation - 1-arylnaphthofurans - one-pot reaction

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References

References and Notes
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Supplementary Material

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