One-Pot Construction of 3-Phthalimido-1,5-benzodiazepine-2-one Derivatives via in situ Activation of N,N-Phthaloyl-serine

The Michael addition of dehydroalanine-activated ester in situ generated from N, N-phthaloyl-serine with o-phenylenediamine followed by cyclization has been established under mild conditions, which afforded 3-phthalimido-1,5-benzodiazepine-2-one derivatives in moderate to good yields.

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Bibliographic Details
Published inSynlett Vol. 29; no. 12; pp. 1639 - 1643
Main Authors Obara, Nobuhiro, Watanabe, Takeshi, Asakawa, Tomohiro, Kan, Toshiyuki, Tanaka, Takao
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 24.07.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
intramolecular amidation
ANTAGONIST
ALPHA,BETA-DEHYDROAMINO ACIDS
3-amino-1
EFFICIENT SYNTHESIS
DEHYDROAMINO ACIDS
RECEPTOR
phenyl-enediamine
5-benzodiazepine-2-one
dehydroalanine
o
DEHYDROPEPTIDES
1ST
in situ generation
one pot synthesis
RING-CLOSING METATHESIS
INHIBITORS
Michael addition reaction
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Summary:The Michael addition of dehydroalanine-activated ester in situ generated from N, N-phthaloyl-serine with o-phenylenediamine followed by cyclization has been established under mild conditions, which afforded 3-phthalimido-1,5-benzodiazepine-2-one derivatives in moderate to good yields.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1610026