Abstract
The condensation of 2-pyrazolin-5-ones with phenyl isothiocyanate, followed by reaction of the resulting thiolate ions with chloroacetyl chloride, phenacyl bromide, oxalyl chloride, 1,4-dibromo-2,3-butanedione and ethyl chloroformate, resulted in cyclisation to S,N-heterocycles in all cases. 2-Iminothiazolidin-4-ones, with phenyl isothiocyanate and then chloroacetyl chloride or phenacyl bromide, similarly formed 2,4′-bi(thiazolidine)-derived products.
References
1.
Mukerjee A.K.
, and
Ashare R.
, Chem. Rev , 1991 , 91 , 1 .
2.
(a)
El-Desoky S.I.
,
Bondock S.B.
,
Etman H.A.
,
Fadda A.A.
, and
Metwally M.A.
, Sulfur Lett. , 2003 , 26 , 127 ; (b) S.I. El-Desoky, H.A. Etman, S.B. Bondock, A.A. Fadda and M.A. Metwally, Sulfur Lett. , 2002, 25 , 199.
3.
öcal N.
,
Aydogan F.
,
Yolacan C.
, and
Turgut Z.
, J. Heterocycl. Chem. , 2003 , 40 , 721 .
4.
Aydogan F.
,
öcal N.
,
Turgut Z.
, and
Yolacan C.
, Bull. Korean Chem. Soc , 2001 , 5 , 476 .
5.
Mendez L.Y.V.
,
Kouznetsov V.
,
Poveda J.C.
,
Yolacan C.
,
öcal N.
, and
Aydogan F.
, Heterocycl. Comm. , 2001 , 7 , 129 .
6.
öcal N.
,
Yolacan C.
,
Kaban S.
,
Mendez L.Y.V.
, and
Kouznetsov V.
, J. Heterocycl. Chem. , 2001 , 38 , 233 .
7.
Abdel-Megid M.
, and
Awas M.A.A.
, Heterocycl. Comm. , 2002 , 8 , 161 .
8.
Hiroyoshi N.
,
Toshiaki W.
,
Satashi Y.
,
Yasuhiro M.
,
Katsuhiko I.
, and
Hiroko S.
, Eur. Pat., E.P. 0208874, 1987 , 1-25.
9.
Ivanova B.B.
,
Chapkanov A.G.
,
Arnaudov M.G.
, and
Petkov I.K.
, Spectrosc. Lett. , 2006 , 39 , 1 .
10.
Ottana R.
,
Maccari R.
,
Barreca M.L.
,
Bruno G.
,
Rotondo A.
,
Rossi A.
,
Chiricosta G.
,
Di Paola R.
,
Sautebin L.
,
Cuzzocrea S.
, and
Vigorita M.G.
, Bioorg. Med. Chem , 2005 , 13 , 4243 .