Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones.

Kremen, Filip; Gazvoda, Martin; Kafka, Stanislav; Proisl, Karel; Srholcová, Anna; Klásek, Antonín; Urankar, Damijana; Kosmrlj, Janez

Kremen, Filip; Gazvoda, Martin; Kafka, Stanislav; Proisl, Karel; Srholcová, Anna; Klásek, Antonín; Urankar, Damijana; Kosmrlj, Janez.

Afiliación

Kremen F; Department of Chemistry, Faculty of Technology, Tomas Bata University , Zlín 76272, Czech Republic.
Gazvoda M; Faculty of Chemistry and Chemical Technology, University of Ljubljana , Vecna pot 113, Ljubljana SI 1000, Slovenia.
Kafka S; Department of Chemistry, Faculty of Technology, Tomas Bata University , Zlín 76272, Czech Republic.
Proisl K; Department of Chemistry, Faculty of Technology, Tomas Bata University , Zlín 76272, Czech Republic.
Srholcová A; Department of Chemistry, Faculty of Technology, Tomas Bata University , Zlín 76272, Czech Republic.
Klásek A; Department of Chemistry, Faculty of Technology, Tomas Bata University , Zlín 76272, Czech Republic.
Urankar D; Faculty of Chemistry and Chemical Technology, University of Ljubljana , Vecna pot 113, Ljubljana SI 1000, Slovenia.
Kosmrlj J; Faculty of Chemistry and Chemical Technology, University of Ljubljana , Vecna pot 113, Ljubljana SI 1000, Slovenia.

J Org Chem ; 82(1): 715-722, 2017 01 06.

Article en En | MEDLINE | ID: mdl-27787977

RESUMEN

An unprecedented reactivity of 3-aminoquinoline-2,4-diones is reported. Under basic conditions, these compounds undergo molecular rearrangement to furnish 1,4-benzodiazepine-2,5-diones. The transformations take place under mild reaction conditions by using 1,1,3,3-tetramethylguanidine, NaOEt, or benzyltrimethylammonium hydroxide as a base. A proposed mechanism of the rearrangement and the conformational equilibrium of 1,4-benzodiazepine-2,5-dione rings are discussed.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2017 Tipo del documento: Article País de afiliación: República Checa Pais de publicación: Estados Unidos

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