Abstract
A novel method for the preparation of N-chloroaldimines from commonly available aromatic aldehydes has been developed. The reaction proceeded effectively by two steps: aldehydes were initially transformed into imines and then chloro-substitution with NaClO2 gave the N-chloroaldimines. This simple protocol allows for the preparation of a variety of aromatic N-chloroaldimines in moderate to excellent yields without the isolation of the imine intermediate. We also found that 3-nitrobenzaldehyde and 4-cyanobenzaldehyde were converted into the related benzonitrile directly under the standard conditions.
References
1.
Kupfer R.
, and
Brinker U.H.
, J. Org. Chem. , 1996 , 61 , 4185 .
2.
Gaspa S.
,
Porcheddu A.
,
Valentoni A.
,
Garroni S.
,
Enzo S.
, and
Luca L.D.
, Eur. J. Org. Chem. , 2017 , 37 , 5519 .
3.
Lemaistre J.W.
,
Rainsford A.E.
, and
Hauser C.R.
, J. Org. Chem. , 1939 , 4 , 106 .
4.
Sun D.
,
Wang Z.
,
Di Y.
,
Jaen J.C.
,
Labelle M.
,
Ma J.
,
Miao S.
,
Sudom A.
,
Tang L.
,
Tomooka C.S.
,
Tu H.
,
Ursu S.
,
Walker N.
,
Yan X.
,
Ye Q.
, and
Powers J.P.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 3513 .
5.
Okamoto O.
,
Kobayashi K.
,
Kawamoto H.
,
Ito S.
,
Yoshizumi T.
,
Yamamoto I.
,
Hashimoto M.
,
Shimizu A.
,
Takahashi H.
,
Ishii Y.
,
Ozaki S.
, and
Ohta H.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 3282 .
6.
Liu J.
,
Xu J.
,
Ren J.
, and
Zeng B.B.
, Chem. Lett. , 2014 , 43 , 190 .
7.
Xiong X.
,
Xu X.
,
Zhou Y.
, and
Weng C.
, Russ. J. Gen. Chem. , 2013 , 83 , 2402 .
8.
Liu J.
,
Zheng H.-X.
,
Yao C.-Z.
,
Sun B.-F.
, and
Kang Y.-B.
, J. Am. Chem. Soc. , 2016 , 138 , 3294 .
9.
Kawagoe Y.
,
Moriyama K.
, and
Togo H.
, Eur. J. Org. Chem. , 2014 , 19 , 4115 .
10.
Hasegawa M.
, Heterocycles , 1998 , 47 , 857 .
11.
Li X.L.
,
Qiu R.
,
Wan W.L.
,
Cheng X.
,
Hai L.
, and
Wu Y.
, Lett. Org. Chem. , 2015 , 12 , 217 .
12.
Zhang J.L.
, Gaodeng Xuexiao Huaxue Xuebao , 1987 , 8 , 246 ; Chem. Abstr. , 1988, 108, 37295.
13.
Hauser C.R.
,
Hauser M.L.
, and
Gillaspie A.
, J. Am. Chem. Soc. , 1930 , 52 , 4158 .
14.
Roux M.V.
,
Jiménez P.
,
Dávalos J.Z.
,
Temprado M.
, and
Liebman J.F.
, J. Chem. Thermodyn. , 2003 , 35 , 803 .
15.
Abraham R.J.
, and
Reid M.
, Magn. Reson. Chem. , 2000 , 38 , 570 .
