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Solid-phase synthesis of trisubstituted guanidines

โœ Scribed by David H. Drewry; Samuel W. Gerritz; James A. Linn


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
233 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The solid-phase synthesis of trisubsituted guanidines is reported via aza-Wittig coupling of a solid-supported alkyl iminophosphorane with an aryl or alkyl isothiocyanate to generate the corresponding solid-supported carbodiimide which is then reacted with a primary or secondary amine to afford the desired trisubst~tuted guanidines.


๐Ÿ“œ SIMILAR VOLUMES


Solid phase synthesis of guanidines
โœ Shaughnessy Robinson; Eric J. Roskamp ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 494 KB
Solid-phase synthesis of disubstituted g
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A method for the solid-phase synthesis of disubstituted guanidines is reported. In this procedure, polymer-bound aryl or alkyl amines are converted to methyl isothioureas in three steps and treated with primary and secondary amines to form the disubstituted guanidine products.

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An efficient method for the solid-phase synthesis of substituted guanidines is presented. A variety of alcohols react with resin-bound N,N'-bis(t-butoxycarbonyl)thiopseudourea under Mitsunobu conditions to give the corresponding alkylated thiopseudoureas. The guanidines are liberated from the resin

Novel linker for the solid-phase synthes
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A novel linker for the generation of alkyl-, acyl-and arylguanidines as an attachment point in solid phase synthesis has been developed. Introduction of a suitably functionalized thiourea to Wang resin via a carbamate linkage, followed by displacement of sulfur with a 1 ยฐ or 2 ยฐ amine affords resin