Efficient preparation of N′,N″-1H-isoindole-1,3-diylidenedicarbohydrazides via 1,1,3-trichloro-1H-isoindole, and their characterization

Unexpected Formation of N-(1-(2-Aryl-hydrazono)isoindolin-2-yl)benzamides and Their Conversion into 1,2-(Bis-1,3,4-oxadiazol-2-yl)benzenes

“…The presence in solution of the two diastereomers could be due either to the existence of geometrical isomers at the exocyclic CN double bond or as a result of the hindered rotation of the C−N amide bond, the latter situation having been previously reported for related N′,N′′-1H-isoindole-1,3-diylidenedicarbohydrazides. 34 To establish the stereochemistry of the two detected diastereoisomers, nuclear Overhauser effects (NOE) have been used (see the Supporting Information). The results clearly indicated the geometrical isomerism at the exocyclic CN bond.…”

Recent Developments in Isoindole Chemistry

“…3 Additional resonance structures can be drawn in which this electron donation places a negative charge on C-5 ( 2b ), where MO calculations have found that the π-electron density is higher than at C-7 ( 2c ). In addition to the reactions described in this review, numerous cycloaddition, 8 9 10 11 12 13 14 15 16 nucleophilic, 12 , 17 18 19 20 and electrophilic 3 15 21 aromatic substitution, Michael addition, 9 intramolecular cyclization, 20 redox, 6 , 22 23 24 25 26 27 and polymerization 15 reactions have been reported. 1 3…”

“…3 Additional resonance structures can be drawn in which this electron donation places a negative charge on C-5 (2b), where MO calculations have found that the -electron density is higher than at C-7 (2c). In addition to the reactions described in this review, numerous cycloaddition, [8][9][10][11][12][13][14][15][16] nucleophilic, 12,[17][18][19][20] and electrophilic 3,15,21 aromatic substitution, Michael addition, 9 intramolecular cyclization, 20 redox, 6,[22][23][24][25][26][27] and polymerization 15 reactions have been reported. 1,3 Due to their highly reactive nature, isoindoles are important synthetic intermediates to their derivatives (Figure 4), such as isoindolines 9, isoindolinones 10, and phthalimides 11.…”

Crystal structure of 4-tert-butyl-2-{2-[N-(3,3-dimethyl-2-oxobutyl)-N-isopropylcarbamoyl]phenyl}-1-isopropyl-1H-imidazol-3-ium perchlorate

“…The title compound was synthesized according to the literature procedure (Hordiyenko et al, 2009). To a stirred solution of 1-(N-isopropylamino)-3,3-dimethylbutan-2-one (10 mmol) in dry CHCl 3 (10 mL), a solution of 1,1,3-trichloro-1H-isoindole (2.5 mmol) in dry CHCl 3 (10 mL) was added dropwise at room temperature under an argon atmosphere.…”