Synthesis 2015; 47(24): 3990-3996
DOI: 10.1055/s-0035-1560268
paper
© Georg Thieme Verlag Stuttgart · New York

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

V. Kameshwara Rao
a  Department of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India   Email: anilkumar@pilani.bits-pilani.ac.in
,
Pinku Kaswan
a  Department of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India   Email: anilkumar@pilani.bits-pilani.ac.in
,
Ganesh M. Shelke
a  Department of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India   Email: anilkumar@pilani.bits-pilani.ac.in
b  Department of Biology and Chemistry, Nipissing University, North Bay, ON, P1B 8L7, Canada
,
Ashley Ryan
b  Department of Biology and Chemistry, Nipissing University, North Bay, ON, P1B 8L7, Canada
,
Mukund Jha
b  Department of Biology and Chemistry, Nipissing University, North Bay, ON, P1B 8L7, Canada
,
Anil Kumar*
a  Department of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India   Email: anilkumar@pilani.bits-pilani.ac.in
› Author Affiliations
Further Information

Publication History

Received: 30 June 2015

Accepted after revision: 24 August 2015

Publication Date:
18 September 2015 (online)


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.

Supporting Information

 
  • References and Notes

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