Facile synthesis of 4-aryl and alkyl substituted, N6-alkylated pyridazine-3, 6-diamines. Issue 48 (2nd December 2015)

• Record Type: Journal Article
• Authors: Wlochal, Joanna; Bailey, Andrew
• Is Part Of: Tetrahedron letters. Volume 56:Issue 48(2015)
• Page Start: 6791
• Page End: 6794
• Publication Date: 2015-12-02
• Subjects: VFCJSNXRXPYHPX-UHFFFAOYSA-N -- FFLVBPUGUYNVPF-UHFFFAOYSA-N -- IWZPBBHWYFWAEO-UHFFFAOYSA-N -- UUWSHOHFXLDAGD-UHFFFAOYSA-N -- ASMOKXYSUMSGRG-UHFFFAOYSA-N -- XLCYMSXJVGTGSL-UHFFFAOYSA-N -- PBXAEQIQOHTLRH-UHFFFAOYSA-N -- ZJYHGQPREYDADV-UHFFFAOYSA-N -- ZSZIEKVYWAXJPS-UHFFFAOYSA-N -- KIDNPRNPAZEDBQ-UHFFFAOYSA-N -- QIUJRWSOGMQALJ-UHFFFAOYSA-N -- MBCTYVUNXBGWLK-UHFFFAOYSA-N -- NASMAWZTONBCNL-UHFFFAOYSA-N -- QEMWJTODHSELFA-UHFFFAOYSA-N -- YQNSOJGOIQWIOG-UHFFFAOYSA-N -- WKTBZNNYCIVDPO-UHFFFAOYSA-N -- IOAWNBZKIWPDOV-UHFFFAOYSA-N -- IQOXFTYBWQRRMR-UHFFFAOYSA-N -- SPLIQKVLUSEKTC-UHFFFAOYSA-N -- PRCDXMDAKGGTJO-UHFFFAOYSA-N -- PAZNGNWQUIPTMI-UHFFFAOYSA-N -- CENBGYHEEUCHPF-UHFFFAOYSA-N -- BEJDKQXUCYAULQ-UHFFFAOYSA-N; Substituted pyridazine-3, 6-diamines -- 3, 6-Diaminopyridazines -- Brettphos precatalyst -- Buchwald protocol; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.10.075
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Substituted pyridazine-3, 6-diamines are attractive but poorly precedented scaffolds in medicinal chemistry and are challenging targets in terms of synthetic tractability. In the following communication we report the use of a Buchwald protocol for the facile synthesis of 4-aryl and alkyl substituted, N 6 -alkylated pyridazine-3, 6-diamines. This approach utilises the unreactive nature of the pyridazine 3-amino group, negating the need for an additional protecting group in the transformation. The relevant precursors were prepared by selective Suzuki or Negishi transformations using commercially available 4-bromo-6-chloro-3-pyridazinamine.