Synlett 2014; 25(11): 1565-1570
DOI: 10.1055/s-0033-1338995
letter
© Georg Thieme Verlag Stuttgart · New York

Redox-Neutral Iron–Sulfur Promoted Transformation of 2-Nitrophenols and 2,6-Disubstituted p-Cresols into 2-Arylbenzoxazoles

Masahiko Saibara*
a   Research Center, Honshu Chemical Industry Co., Ltd., 2-5-115, Kozaika, Wakayama 641-0007, Japan
,
Kazuhito Ashida
a   Research Center, Honshu Chemical Industry Co., Ltd., 2-5-115, Kozaika, Wakayama 641-0007, Japan
,
Kouji Satomi
a   Research Center, Honshu Chemical Industry Co., Ltd., 2-5-115, Kozaika, Wakayama 641-0007, Japan
,
Toshiyuki Iwai
b   Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan   Fax: +81(6)69638030   eMail: tmizuno@omtri.or.jp
,
Takeo Nakai
b   Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan   Fax: +81(6)69638030   eMail: tmizuno@omtri.or.jp
,
Masatoshi Mihara
b   Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan   Fax: +81(6)69638030   eMail: tmizuno@omtri.or.jp
,
Takatoshi Ito
b   Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan   Fax: +81(6)69638030   eMail: tmizuno@omtri.or.jp
,
Takumi Mizuno*
b   Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan   Fax: +81(6)69638030   eMail: tmizuno@omtri.or.jp
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Publikationsverlauf

Received: 03. März 2014

Accepted after revision: 06. April 2014

Publikationsdatum:
20. Mai 2014 (online)


Abstract

A catalyst based on iron and elemental sulfur has been shown to efficiently promote a redox-neutral reaction between 2-nitrophenols and 2,6-disubstituted p-cresols, allowing for the preparation of 2-arylbenzoxazoles in good yields. This synthetic methodology also affords high atom economy without the use of any external oxidizing and/or reducing reagents. This is the first redox–condensation reaction of 2-nitrophenols with 2,6-disubstituted p-cresols.

Supporting Information