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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Combinatorial synthesis of heterocycles: solid-phase synthesis of 6-amino-2,4-dioxo-3,4-dihydro-1,3,5-triazine
1Chemical Sciences Division, Wyeth-Ayerst Research, Pearl River, New York 10965, USA.
Abstract:
A new solid-phase synthesis of trisubstituted 6-amino-2,4-dioxo-3,4-dihydro-1,3,5-triazines from a resin-bound amine component is described. The amine was readily converted to the corresponding polymer-bound S-methylthiopseudourea, which upon reaction with secondary amines gave the disubstituted guanidines. Cyclization of the polymer-bound guanidines with chlorocarbonylisocyanate afforded the triazinediones. The third point of diversity was introduced by the Mitsunobu reaction. The method is amenable for iterative combinatorial library generation.
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