Catalyst-Controlled Regioselective Synthesis of Benzotriazlolodiazepin-7-ones and Benzotriazolodiazocin-8-ones

A catalyst-controlled highly chemoselective and regioselective intramolecular cycloamidation of triazol-1-ylbenzamides toward the synthesis of scarcely known heterocycles is reported. In the presence of a palladium catalyst, this cycloisomerization reaction afforded substituted benzotriazlolodiazepi...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 2; pp. 428 - 432
Main Authors Chen, Kai-Chi, Barve, Indrajeet J, Sun, Chung-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.01.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INSOMNIA
PEPTIDES
ENTRY
STRATEGY
CONSTRUCTION
EXPANSION
LACTAMS
ALKYNES
EFFICIENT
CYCLIZATION
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Summary:A catalyst-controlled highly chemoselective and regioselective intramolecular cycloamidation of triazol-1-ylbenzamides toward the synthesis of scarcely known heterocycles is reported. In the presence of a palladium catalyst, this cycloisomerization reaction afforded substituted benzotriazlolodiazepin-7-ones via intramolecular insertion of a palladium into C–C triple bond in a 7-exo-dig way. Alternatively, the use of a silver catalyst in the reaction produced substituted benzotriazolodiazocin-8-ones in a highly regioselective manner through 8-endo-dig intramolecular ring closure.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04162