Novel syntheses of 1,4-benzodiazepines, isoindolo[2,1-d][1,4]benzodiazepines, isoindolo[1,2-a][2]benzazepines, and indolo[2,3-d][2]benzazepines, based on use of the Strecker reaction

Walker, Gordon N.; Engle, Allan R.; Kempton, Robert J.

doi:10.1021/jo00797a001

Cited by 33 publications

(12 citation statements)

References 9 publications

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“…Of the heterocycles 1-4 only compound 4 has been studied sufficiently at the present time. Information on methods for the construction of and the chemical characteristics of the polycycles 1 and 2 can be gleaned from a limited number of publications [1][2][3][4]. We were only able to find mention of derivatives of isoindolo[2,1-b]benz-2-azepines 3 in nine papers [5][6][7][8][9][10][11][12][13], four of which are patents (10-13).…”

Section: Isoindolobenzazepinesmentioning

confidence: 99%

“…There have only been data on methods for the synthesis of isoindolo[1,2-a]benz-2-azepines in four publications [2][3][4]69].…”

Section: Synthesis Of Isoindolo[12-a]benz-2-azepinesmentioning

confidence: 99%

“…Isoindolo[1,2-a]benz-2-azepines can be obtained from 3-(γ-arylpropylamino)phthalides [2][3][4]. Thus, under the influence of PPA 3-(γ-phenylpropylamino)phthalide 83 undergoes cyclization to the corresponding isoindolo[1,2-a]benz-2-azepine 84 [2].…”

Section: Synthesis Of Isoindolo[12-a]benz-2-azepinesmentioning

confidence: 99%

“…Thus, under the influence of PPA 3-(γ-phenylpropylamino)phthalide 83 undergoes cyclization to the corresponding isoindolo[1,2-a]benz-2-azepine 84 [2]. A similar method involves the reaction of 3-[γ- (3,4-dimethoxyphenyl)propylamino]phthalide 85 with thionyl chloride or pyrophosphoryl chloride to form the phthalimidine 86.…”

Section: Synthesis Of Isoindolo[12-a]benz-2-azepinesmentioning

confidence: 99%

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mentioning

confidence: 99%

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

Boltukhina

Zubkov

Varlamov

2006

Chem Heterocycl Compd

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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 1959Data for -2004 The interest in the development of methods for the synthesis of tetracyclic structures in which an isoindole fragment is annelated with quinoline, isoquinoline, or benzazepine fragments is due to the wide spectrum of physiological activity and the widespread occurrence of such structures in nature.In spite of the considerable amount of experimental data there are no papers summarizing methods for the construction of such structures.In the present review data on the synthesis of isoindolobenz-3-and isoindolobenz-2-azepines, isoindoloazocines, isoindoloquinolines, and isoindoloisoquinolines are examined systematically. The review is structured in this way because isoindolo[1,2-b]benz-3-azepines form the main structural fragment in a large number of alkaloids and the available information on their synthesis is the most comprehensive. In addition to the methods of synthesis, the review contains certain information on the occurrence of the condensed isoindoles in nature and on their physiological activity.

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