Heterocyclic Merging of Stereochemically Diverse Chiral Piperazines and Morpholines with Indazoles.
chiral morpholines
chiral piperazines
fused heterocycles
indazoles
scaffold merging
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Oct 2023
02 Oct 2023
Historique:
received:
13
06
2023
medline:
18
7
2023
pubmed:
18
7
2023
entrez:
18
7
2023
Statut:
ppublish
Résumé
We report a heterocyclic merging approach to construct novel indazolo-piperazines and indazolo-morpholines. Starting from chiral diamines and amino alcohols, novel regiochemically (1,3 and 1,4) and stereochemically diverse (relative and absolute) cohorts of indazolo-piperazines and indazolo-morpholines were obtained within six or seven steps. The key transformations involved are a Smiles rearrangement to generate the indazole core structure and a late-stage Michael addition to build the piperazine and morpholine heterocycles. We further explored additional vector diversity by incorporating substitutions on the indazole aromatic ring, generating a total of 20 unique, enantiomerically pure heterocyclic scaffolds.
Identifiants
pubmed: 37462979
doi: 10.1002/chem.202301888
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301888Subventions
Organisme : NIGMS NIH HHS
ID : R01GM139295
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01GM139295
Pays : United States
Organisme : Bill & Melinda Gates Foundation
ID : INV-001902
Pays : United States
Informations de copyright
© 2023 Wiley-VCH GmbH.
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