Combinatorial synthesis of heterocycles: solid-phase synthesis of 6-amino-2,4-dioxo-3,4-dihydro-1,3,5-triazine derivatives.
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.
Gopalsamy
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A
Chemical Sciences Division, Wyeth-Ayerst Research, Pearl River, New York 10965, USA.
Yang
H
H
D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D006146:Guanidines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013890:Thiourea / Q000737:chemistry; D014227:Triazines / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D000596:Amino Acids; D001565:Benzoates; D006146:Guanidines; D014227:Triazines; D013890:Thiourea