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Synlett 2014; 25(11): 1571-1576
DOI: 10.1055/s-0033-1339026
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of 4H-Chromenes by Tandem Benzylation and Cyclization in the Presence of Sodium Bisulfate on Silica Gel

Tadashi Aoyama*
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan   Fax: +81(3)32590818   eMail: aoyama.tadashi@nihon-u.ac.jp
b   The Center for Creative Materials Research, Research Institute of Science and Technology, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
,
Takumi Yamamoto
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan   Fax: +81(3)32590818   eMail: aoyama.tadashi@nihon-u.ac.jp
,
Saki Miyota
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan   Fax: +81(3)32590818   eMail: aoyama.tadashi@nihon-u.ac.jp
,
Mamiko Hayakawa
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan   Fax: +81(3)32590818   eMail: aoyama.tadashi@nihon-u.ac.jp
,
Toshio Takido
,
Mitsuo Kodomari
c   The Institute of Natural Sciences, College of Humanities and Science, Nihon University, Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan
› Institutsangaben
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Publikationsverlauf

Received: 05. März 2014

Accepted after revision: 06. April 2014

Publikationsdatum:
20. Mai 2014 (online)

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Abstract

A simple and efficient method has been developed for the synthesis of 4H-chromenes from o-hydroxybenzylic alcohols and dicarbonyl compounds containing active methylene groups by using silica gel supported sodium bisulfate. Various dicarbonyl compounds such as diketones, keto esters, and keto amides can be used in the synthesis of the 4H-chromenes.

Key words

cyclizations - benzylations - supported reagents - chromenes - one-pot syntheses

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
  • Supporting Information