2-[(Z)-4,7-Dichloro-3,3-dimethyl-2,3-dihydro-1H-indol-2-ylidene]-3-oxopropanenitrile

Abstract

In the title compound, C13H10Cl2N2O, the ring N atom and its three attached atoms are essentially coplanar with angles adding to 359.8°, indicating conjugation with the 2-formyl­acrylonitrile subunit. The aldehyde group is oriented to place the carbonyl O atom 2.02 (3) Å from the N—H hydrogen atom. Intra­molecular N—H⋯O and C—H⋯Cl inter­actions occur. The geometry of the exocyclic double bond is Z. In the crystal, weak C—H⋯N hydrogen bonds link the mol­ecules into chains along [10].

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

“…1 and 2, respectively. Corresponding bond distances and angles of the isatin ring systems in (I) and (II) are essentially equivalent and comparable with those in related structures (Helliwell et al, 2012;Lö tter et al, 2007). A superposition of the isatin ring systems in (I) and (II) ( Fig.…”

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

“…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 . The bond lengths and bond angles of the isatin moiety of compound (I) are also comparable with the values observed for related structures (Helliwell et al, 2012;Lö tter et al, 2007). The sum of the angles around the N atom is 360 , indicating the absence of an sp 3 lone pair.…”

Spiro[4H‐pyran‐3,3′‐oxindoles] Derived from 1,2,3,4‐Tetrahydroquinoline

“…C-NMR spectra were recorded on a Bruker Avance AQS (300 and 400 MHz) spectrometer, at (300, 400 MHz and 75, 100 MHz), respectively. Chemical shifts δ are in parts per million (ppm) measured in CDCl 3 and DMSO-d 6 as solvent and relative to TMS as the internal standard. Infrared spectra were recorded on a Thermonicolet-Nexus 670 Fourier transform infrared instrument.…”

“…The cyclocondensation reaction between a ketone, malononitrile (or a cyanoacetate), and a 1,3‐diketone, generating a 2‐amino‐4 H ‐pyran‐3‐carbonitrile (or 3‐carboxylate) has been often exemplified. In the context of our continuing studies of various aspects of indole chemistry , we noted that this 4 H ‐pyran‐constructing sequence has in particular been applied several times to isatin (1 H ‐indole‐2,3‐dione) in which the 3‐carbonyl group plays the role of the ketone in the three‐component process. Scheme shows the domino‐Knoevenagel‐Michael sequence of events using isatin, malononitrile, and a generalized 1,3‐diketone (the initial Knovenagel condensation can be conducted separately before interaction with the 1,3‐diketone).…”