Affiliation:
1. Verna and Marrs McLean Department of Biochemistry and Molecular Pharmacology Baylor College of Medicine One Baylor Plaza Houston TX 77030 USA
2. Department of Chemistry Rice University 6100 Main Street Houston TX 77005 USA
3. Center for Drug Discovery Department of Pathology and Immunology Baylor College of Medicine One Baylor Plaza Houston TX 77030 USA
Abstract
AbstractWe 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.
Funder
National Institute of General Medical Sciences
Cancer Prevention and Research Institute of Texas
Welch Foundation
Subject
General Chemistry,Catalysis,Organic Chemistry