Annulation of Primary Amines to Piperazines and Diazaspirocycles Utilizing α-Methyl Benzyl Resin
Authors:
- 19 November 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of Combinatorial Chemistry
- Vol. 8 (1) , 132-140
Abstract
The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates. Critical to the success of this chemistry was the development of alpha-methyl benzyl carbamate resin linker. This resin permits the cleavage of the heterocycles under mildly acidic conditions, free of contaminating linker-derived N-alkylated byproducts.Keywords
This publication has 10 references indexed in Scilit:
- Solid/Solution‐Phase Annulation Reagents: Single‐Step Synthesis of Cyclic Amine DerivativesAngewandte Chemie International Edition, 2005
- Colorimetric Monitoring of Solid-Phase Aldehydes Using 2,4-DinitrophenylhydrazineJournal of Combinatorial Chemistry, 2004
- Solid-Phase Synthesis of 1,2,3-Triazoles via 1,3-Dipolar CycloadditionJournal of Combinatorial Chemistry, 2003
- The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged SubstructuresChemical Reviews, 2003
- The Solid-Phase Synthesis and Use of N-Monosubstituted Piperazines in Chemical Library SynthesisJournal of Combinatorial Chemistry, 2003
- Spirocyclic nonpeptide glycoprotein IIb–IIIa antagonists. Part 1: design of potent and specific 3,9-diazaspiro[5.5]undecanesBioorganic & Medicinal Chemistry Letters, 2001
- 5-HT3 Antagonists Derived from Aminopyridazine-type Muscarinic M1 AgonistsJournal of Medicinal Chemistry, 1998
- A new cleavage strategy for the solid-phase synthesis of secondary aminesTetrahedron Letters, 1997
- Facile Preparation of 2,6-Disubstituted Purines Using Solid-Phase ChemistryThe Journal of Organic Chemistry, 1997
- A potent new class of .kappa.-receptor agonist: 4-substituted 1-(arylacetyl)-2-[(dialkylamino)methyl]piperazinesJournal of Medicinal Chemistry, 1993