Abstract
The mechanism of a DMF-catalysed electrophilic/nucleophilic chlorination of pyrazole is illustrated with the aid of calculations of the natural bonding orbital charges. Its high regioselectivity and good functionality tolerance of nine pyrazole substrates have been experimentally demonstrated.
Keywords
References
1.
Devine G.J.
,
Barber M.
, and
Denholm I.
, Pest Manag. Sci. , 2001 , 57 , 443 .
2.
Suzuki S.
, and
Yoshitani K.
, Japanese patent 09194305, 1997; Chem. Abstr. , 1997 , 127 , 157969 .
3.
Miura Y.
,
Ohnishi M.
,
Mabuchi T.
, and
Yanai I.
, Brighton Crop Prot. Conf. Weeds , 1993 , 1 , 35 .
4.
Stierli D.
,
Daina A.
,
Walter H.
,
Tobler H.
, and
Rajan R.
, WO patent 2009012998, 2009; Chem. Abstr. , 2009 , 150 , 214379 .
5.
Moedritzer K.
, and
Rogers M.D.
, European patent 371947, 1990; Chem. Abstr. , 1990 , 113 , 211973 .
6.
Chen H.
,
Li Z.
, and
Han Y.
, J. Agric. Food Chem. , 2000 , 48 , 5312 .
7.
Kinzel T.
,
Zhang Y.
, and
Buchwald S.L.
, J. Am. Chem. Soc. , 2010 , 132 , 14073 .
8.
Baffoe J.
,
Hoe M.Y.
, and
Toure B.B.
, Org. Lett. , 2010 , 12 , 1532 .
9.
Guram A.S.
,
King A.O.
,
Allen J.G.
,
Wang X.
,
Schenkel L.B.
,
Chan J.
,
Bunel E.E.
,
Faul M.M.
,
Larsen R.D.
,
Martinelli M.J.
, and
Reider P.J.
, Org. Lett. , 2006 , 8 , 1787 .
10.
Zhao Z.
, and
Wang Z.
, Synth. Commun. , 2007 , 37 , 137 .
11.
Varano F.
,
Catarzi D.
,
Colotta V.
,
Calabri F.R.
,
Lenzi O.
,
Filacchioni G.
,
Galli A.
,
Costagli C.
,
Deflorian F.
, and
Moro S.
, Bioorg. Med. Chem. , 2005 , 13 , 5536 .
12.
O'Brien D.F.
, and
Gates J.W.
Jr.
, J. Org. Chem. , 1966 , 31 , 1538 .
13.
Lutze G.
,
Kirschke K.
, and
Krauss N.
, J. Prakt. Chem./Chem.-Ztg. , 1993 , 335 , 616 .
14.
Zhang X.
,
Zhu H.
,
Tan H.
,
Ni J.
,
He H.
,
Zeng X.
,
Liu L.
,
Zhang Y.
,
Zhou Y.
,
Feng H.
, J. Shi and N. Wang, Chinese patent 101735199, 2010; Chem. Abstr. , 2010 , 153 , 174961 .
15.
Batterjee S.M.
, Tinctoria , 2002 , 99 , 26 .
16.
Liu Y.
,
He G.
,
Chen K.
,
Jin Y.
,
Li Y.
, and
Zhu H.
, Eur. J. Org. Chem. , 2011 , 5323 .
17.
Li Y.
,
Liu R.
,
Yan Z.
,
Zhang X.
, and
Zhu H.
, Bull. Korean Chem. Soc. , 2010 , 31 , 3341 .
18.
Anandarajagopal K.
,
Anbu Jeba Sunilson J.
,
Illavarasu A.
,
Thangavelpandian N.
, and
Kalirajan R.
, Int. J. Chem. Tech. Res. , 2010 , 2 , 45 .
19.
Li Y.
,
Liu Y.
,
Chen N.
,
Lv K.
,
Xiong X.
, and
Li J.
, HeIv. Chim. Acta , 2014 , 97 , 1269 .
20.
Sheldrick G.M.
, Acta Crystallogr., Sect. A , 2008 , 64 , 112 .
21.
Hariharan P.C.
, and
Pople J.A.
, Theor. Chim. Acta , 1973 , 28 , 213 .
22.
Li Y.
,
Liu Y.
,
Wang H.
,
Xiong X.
,
Wei P.
, and
Li F.
, Molecules , 2013 , 18 , 877 .