A Convenient Deoxygenation-Dimerization-[1+2]-Cycloaddition Synthetic Sequence from ω-Bromoalkylisatins to Indolin-2-onemethanofullerenes Bearing Isoindigo Moiety

Abstract

An easy and convenient step-by-step synthetic procedure towards the design of a novel spiroindolomethanofullerene bearing an isoindigo fragment is reported.

Design and synthesis of new functionalized isoindigo and (3Z,3′Z)-3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) derivatives

“…In general, N-alkyl isoindigo compounds are prepared by the reaction alkyl halides with isoindigo in the presence of potassium carbonate under thermal conditions (100 °C) [22]. In addition, the reaction of haloalkyl isatins with tris(diethylamino)phosphine at low temperature (-60 °C) forms isoindigo compounds with two haloalkyl functional groups [23][24][25]. Due to the wisespread applications of substituted isoindigos, we investigated the breadth of N,N'-disubstituted analogs, with subsequent reactions to extend the catalogue of possible derivatives -this included an array of chains or rings bearing bromo, chloro, nitrile, benzyl ether, allyl, alkene, cyclohexene, and cyclohexane.…”

Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of 2-(1-decyl-2-oxoindolin-3-ylidene)propanedinitrile

“…Search fragment and related compounds. et al, 2014) and (CH 2 ) 3 CH 3 (Yuan & Fang, 2011), (CH 2 ) 6 Br Bogdanov et al, 2013)]. In these, the indole fragment varies from being planar to having a dihedral angle between the two constituent rings of up to 3.30 .…”