Ekaterina V. Boltukhina

A general strategy for the synthesis of oxoisoindolo[2,1-a]quinoline derivatives: the first efficient synthesis of 5,6,6a,11-tetrahydro-11-oxoisoindolo[2,1-a]quinoline-10-carboxylic acids

An efficient two-step synthesis of new isoindolo[2,1-a]quinoline-10-carboxylic acids via [4+2] cycloaddition of the 4-α-furyl-4-N-arylaminobut-1-enes and maleic anhydride is described.

Preparative Synthesis of 7-Carboxy-2-R-isoindol-1-ones

A preparative method for the synthesis of 7-carboxy-2-R-isoindol-1-ones was developed on the basis of the [4+2] cycloaddition of secondary furfurylamines to maleic anhydride.

Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 1. Isoindolobenzazepines, isoindolobenzazocines. (Review)

Data on methods for the construction of tetracyclic systems in which an isoindole ring is condensed with benzazepines and benzazocines on the [1,2] side are reviewed. The reaction conditions and approaches leading to isoindolobenzazepines and isoindolobenzazocines are discussed. Examples of the synthesis of physiologically active natural alkaloids with the structure of the above-mentioned condensed isoindoles are presented. Data for 1959–2004 are included.

Study of regioselectivity of intramolecular cyclization of N-(m-R-phenyl)- and N-(α-naphthyl)-2-allyl(methallyl)-6-carboxy-4-oxo-3-aza-10-oxatricyclo[5.2.1.01,5]dec-8-enes

Regioselectivity of the intramolecular electrophilic substitution in a series of N-(m-R-phenyl)- and N-(α-naphthyl)-2-allyl(methallyl)-6-carboxy-4-oxo-3-aza-10-oxatricyclo[5.2.1.01,5]dec-8-enes in reactions with phosphoric acid was studied. The reactions of N-(m-R-phenyl)-substituted derivatives proceed nonregioselectively to form mixtures of 2-R- and 4-R-substituted isoindolo[2,1-a]quinolines, whereas the reactions of N-(α-naphthyl)-substituted derivatives occur regioselectively at the β position of the naphthyl fragment.

Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 2. Isoindoloquinolines, isoindoloisoquinolines. (Review)

Data for 1966–2004 on methods for the construction of tetracyclic systems in which an isoindole ring is condensed with quinoline and isoquinoline fragments on the [1,2] side are reviewed. Methods and conditions for the synthesis of isoindoloquinolines and isoindoloisoquinolines are examined. Examples of the synthesis of physiologically active natural alkaloids possessing the structure of these condensed isoindoles are presented.

Novel preparative method for synthesis of isoindolo[2,1-b]benz-2-azepine-8-carboxylic acids

Based on readily accessible homoallyl amines, we previously developed preparative methods for synthesis of substituted and spiro-annelated tetrahydroquinolines [1], 3-aza-11-oxatricyclo[6.2.1.01,6]undec-9enes (6,8a-epoxy isoquinolines) [2], γ-piperidoles [3], benz-2-azepines [4], isoindolo[2,1-a]quinoline-10carboxylic acids [5]. In continuing our work on studying the synthetic possibilities for furyl-substituted homoallyl amines, we carried out an original two-step synthesis for isoindolo[2,1-b]benz-2-azepine 3.