Abstract
An economic four-step synthesis of 2,6-dimethoxy-1,4-benzoquinone was achieved in 68% overall yield starting from aniline. The reaction sequence involved conversion to 1,3,5-tribromoaniline, deamination, methoxylation, and oxidation. The procedure is operationally simple and amenable to scale-up production.
References
1.
Lee T.H.
,
Chiou J.L.
,
Lee C.K.
, and
Kuo Y.H.
, J. Chin. Chem. Soc.,(Taipei) , 2005 , 52 , 833 .
2.
Karaket N.
,
Supaibulwatana K.
,
Ounsuk S.
,
Bultel-Ponce V.
,
Pham V.C.
, and
Bodo B.
, Nat. Prod. Commun. , 2012 , 7 , 169 .
3.
Harasawa A.
, and
Tagashira A.
, Biosci. Biotech. Biochem. , 1994 , 58 , 2073 .
4.
Park J.H.
,
Shim K.S.
, and
Lee H.S.
, J. Korean Soc. Appl. Biol. Chem. , 2014 , 57 , 699 .
5.
Lee S.Y.
,
Suh W.S.
,
Cha J.M.
,
Moon E.
,
Ha S.K.
,
Kim S.Y.
, and
Lee K.R.
, Phytochem. Lett. , 2016 , 17 , 79 .
6.
Kwon H.C.
,
Choi S.U.
, and
Lee K.R.
, Arch. Pharm. Res. , 2001 , 24 , 312 .
7.
Kuo H.T.
,
Peng C.F.
,
Huang H.Y.
,
Lin C.H.
,
Chen I.S.
, and
Tsai I.L.
, Planta Med. , 2011 , 77 , 736 .
8.
Kim M.H.
,
Jo S.H.
,
Ha K.S.
,
Song J.H.
,
Jang H.D.
, and
Kwon Y.I.
, J. Microbiol. Biotechn. , 2010 , 20 , 1204 .
9.
Yoo J.G.
,
Kim D.H.
,
Park E.H.
,
Lee J.S.
,
Kim S.Y.
, and
Kim M.D.
, J. Korean Soc. Appl. Biol. Chem. , 2011 , 54 , 795 .
10.
Choi E.J.
,
Ka E.H.
,
Jo C.Y.
,
Jo S.H.
,
Apostolidis E.
,
Lee M.S.
,
Jang H.D.
, and
Kwon Y.I.
, Food Sci. Biotechnol. , 2014 , 23 , 791 .
11.
Lana E.J.L.
,
Carazza F.
, and
Takahashi J.A.
, J. Agr. Food Chem. , 2006 , 54 , 2053 .
12.
Gu L.
, and
Zhong Y.
, Youji Huaxue , 1989 , 9 , 239 .
13.
Nishina A.
, and
Uchibori T.
, Agric. Biol. Chem. , 1991 , 55 , 2395 .
14.
Dimmel D.R.
,
Kuroda K.
,
Pan X.
, and
Bozell J.J.
, J. Wood Chem. Technol. , 1997 , 17 , 235 .
15.
Bozell J.J.
,
Hoberg J.O.
, and
Dimmel D.R.
, Tetrahedron Lett. , 1998 , 39 , 2261 .
16.
Yang J.
, and
Zheng H.
, Huaxi Yaoxue Zazhi , 2006 , 21 , 352 .
17.
Khosravi K.
, and
Kazemi S.
, Chin. Chem. Lett. , 2012 , 23 , 387 .
18.
Coleman G.H.
, and
Talbot W.F.
, Org. Synth. , 1933 , 13 , 96 .
19.
Bharate S.B.
,
Mudududdla R.
,
Sharma R.
, and
Vishwakarma R.A.
, Tetrahedron Lett. , 2013 , 54 , 2913 .