AbstractThe preparation of the title compounds, starting materials for potentially DNA‐intercalating heterocyclic systems, is achieved starting from recently reported indolizinediones via Semmler—Wolff transposition of the corresponding oximes.

The synthesis of new condensed indolizinediones derived from pyroglutamic acid is described. The Semmler-Wolff transposition of the oxime of these ketones leads to fused dihydro-1,5-naphthyridinones. Easy introduction of side amino chains indicates that potential DNA-intercalating heterocyclic systems fused on 1,5-naphthyridine nucleus could be obtained in these series. (c) 2012 Elsevier Ltd. All rights reserved.

The synthesis of some condensed indolizinediones derived from pyroglutamic acid is described. Treatment of these ketones in HCl, HBr or MeONa/MeOH furnished aryl propionic acid derivatives. During the ketone transformations, two sequential processes could take place in competitive manner to provide heterocyclic systems bearing carboxylic acid or hydroxycarboxylic acid function. Easy synthesis of amides indicates that potential DNA-intercalating heterocyclic systems fused on γ-carboline and isoquinoline nucleus could be obtained from these series.

Air oxidation of hexahydrobenz[f]indolizine-3,10-diones in MeOH/MeONa yields alcohols, which are easily and selectively transformed, in very good yields, to succinimides, isoquinoline propanoic acids or dehydrated to ene lactams.

Depending upon the conditions, heating of 1,10a-dihydro-2H,5H-pyrrolo-[1,2-b]isoquinoline-3,10-diones in polyphosphoric or hydrochloric acid gives rise to hydride transfer and oxidative processes. Mono or dienyl lactams, or mixtures of dimers and acids or hydroxyacids of the isoquinotine series were thus formed. Procedures leading specifically to each of these products have been found.

When carried out in methylene dichloride, the Friedel-Crafts cyclization of N-arylmethyl pyroglutamates call lead to addition of a CH2OH group ill the position of. to the newly formed ketone function. (C) 2004 Elsevier Ltd. All rights reserved.

Low solubility of the aromatic aldehyde in a water/ethanol medium can prevent the sodium borohydride reductive alkylation of the sodium salt of glutamic acid. In that case, the reductive alkylation can be realized in methanol by using a triethylammonium salt. The uses of 2 molar equivalent of triethylarnmonium salt of glutamic acid for one molar equivalent of aldehyde strongly raise the yields. Cyclization of the N-substituted glutamic acids obtained gives then N-arylmethyl pyroglutamic acids in good yields.

In the course of a study of keto lactams, treatment of 8-chloro1,10-a- dihydropyrrolo[1,2-b] isoquinoline-3,10(2H,5H)-dione with concentrated hydrochloric acid was realised. The packing of the resultant dimeric compound, C24H18N2O2Cl2, is governed by the formation of pi-stacking interactions.

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

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In the course of a study on pyrrolidinone-derived anticancer agents, the crystal structure of the title compound, 1,1'-(4-methylbenzylidene)bis(5-oxopyrrolidine-2-carboxylic acid), C18H20N2O6, was determined. In this compound, a pi-pi interaction brings the first carboxylic acid group above the aromatic ring, whereas the second carboxylic acid group is oriented above one of the pyrrolidine rings.