Solid-phase synthesis of trisubstituted guanidines
โ 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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โฆ 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.
๐ SIMILAR VOLUMES
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.
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
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