Two new isatin derivatives: 1-benzyl-4,5,6-trimethoxyindoline-2,3-dione and 1-benzyl-5-fluoroindoline-2,3-dione

Abstract

Isatin (1H-indole-2,3-dione) derivatives represent synthetically useful substrates which can be used to prepare a broad range of heterocyclic compounds. In the title compounds, C18H17NO5, (I), and C15H10FNO2, (II), the isatin ring systems are planar and form a dihedral angle of 73.04 (7)° in (I) and 76.82 (11)° in (II) with the benzyl groups. The bicyclic scaffolds in both compounds are almost superimposable, with an r.m.s. deviation of 0.061 Å. The crystal structures of both derivatives are stabilized by C-H···O interactions. These contacts generate an R(1)2(7) ring motif in (I) and a C(7) chain motif in (II).

1-Benzyl-5-methylindoline-2,3-dione

“…Its mean plane makes a dihedral angle of 74.19 (12) with the benzyl ring (C10-C15). This is similar to the values observed in data reports related structures, for example {1-benzyl-4,5,6-trimethoxyindoline-2,3-dione (II), [73.04 7] and 1-benzyl-5-fluoroindoline-2,3-dione (III), [76.82 (11) ]} (Sharmila et al, 2015). The superimposed fit (Gans & Shalloway, 2001) of the isatin group of the title compound (I) (atoms C1-C8, N1, O1 and O2) gives an r.m.s deviation of 0.065 Å with molecule (II) and 0.034 Å with molecule (III), while that with its energy-minimized counterpart gives 0.057 Å .…”

6-Chloro-1-phenylindoline-2,3-dione: absolute structure, non-linear optical and charge-transport properties

“…The crystal structures of many isatin derivatives have been reported, among the analogues of the title compound are 6-bromo-1-butylindoline-2,3-dione (Ji et al, 2009), 1-ethyl-5iodoindoline-2,3-dione (Wang et al, 2014), 6-chloroindoline-2,3-dione (Golen & Manke, 2016), 1-benzyl-5-fluoroindoline-2,3-dione (Sharmila et al, 2015) and 1-phenylindoline-2,3dione (Shukla & Rajeswaran, 2011). The synthesis of the title compound was reported in 2014 (Bergman & Stensland, 2014).…”