Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 7. Cyclisation of amino acid derived α-phtnalimidoacyl ylides to give pyrroloisoindolediones

Ionic liquid-catalyzed and microwave-assisted syntheses of pyrrolizine- and indolizinedione derivatives

“…Yield 98 mg (53%) (a), 113 mg (61%) (b), 133 mg (72%) (c), 157 mg (85%) (d). The physicochemical parameters of Va were consistent with published data [19].…”

“…The structure of compounds Va, Vb, VIa, and Vb was confirmed by spectral methods; the physicochemical parameters of Va were consistent with published data [19]. The 1 H NMR spectra of Va, Vb, VIa, and Vb displayed symmetry violation for two multiplet signals from four protons in the phthaloyl fragment in the region δ 7.46-8.32 (Vb), 7.49-9.15 (VIa), and 7.07-9.18 ppm (VIb), a singlet from protons in the methyl group was observed at δ 1.58 (Vb) and 2.55 ppm (VIb), and the 12-H proton in VIa resonated as a singlet at δ 6.76 ppm.…”

The Usefulness of Phosphorus Compounds in Alkyne Synthesis

“…With the same technique, a number of functionalized alkynes were prepared in moderate yields including, benzofurans via the 2-methoxyphenylalkynes and benzothiophenes via 2-methylthiophenylalkynes, 85,86 diacylalkynes, 87,88 terminal 1,3-diynes, 89 and unsymmetrical 1,3-diynes, 90 1,3-enynes, 91 pyrroloisoindolediones, 92 styrylalkynes, substituted naphthalenes, 93,94 and protected acetylenic amino acids. 95 The limit of the usefulness of the FVP technique was reached with the pyrolysis of the tetraoxo ylides and hexaoxo bis(ylides).…”

Synthesis of pyridazinedione derivatives starting from anhydrides of 2,3-pyridine- and 2,3-quinolinedicarboxylic acids

“…It was shown formerly [6][7][8][9] thet keto-stabilized phosphonium ylides prepared from the N-protected α-and β-amino acids underwent the intramolecular cyclization. We performed through phosphorus ylides the preparation of products I, II with a pyridazinedione fragment starting from 2,3-pyridine-and 2,3-quinolinedicarboxylic acids anhydrides.…”