3-chlorioden-1-ones and related compounds 3-chloro derivatives of 2- [phenyl, 1-naphthyl and 2'-pyridyl] inden-1- one and their reactions

ABSTRACT

The use of certain indandione derivatives as hypoprothrombinemic and anticoagulant led the authors to prepare some of its homologues. 3-chloro-2-phenyl, 3-chloro-2 [1'-naphthyl]- and 3-chloro-2- [2'-pyridyl]-inden-l-one [I-HI] respectively were prepared by the interaction of the corresponding 1, 3-diones with phosphorous oxychloride. The structure of these products were established by elemental analysis, IR spectra [CO at 1700 cm[-1], C=C at 1620 cm[-1] and C-Cl at 750 cm[-1] and analogy with chlorination of indandione. The reactivity of the chlorine atom was established by the condensation of [I-III] with primary, secondary amines and sulpha derivatives which produced the corresponding derivatives [IVa-s], [Va-k], [Vla-k], [VIIa-e], [VIIIa, b] and [IXa, b] respectively