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

Authors

  • 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
Weitere Informationen

Publikationsverlauf

Received: 30. Juni 2015

Accepted after revision: 24. August 2015

Publikationsdatum:
18. September 2015 (online)


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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.

Supporting Information