Solid-phase synthesis of substituted guanidines using a novel acid labile linker |
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Authors: | Pátek M Smrcina M Nakanishi E Izawa H |
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Institution: | Selectide Corporation, a subsidiary of Aventis Pharmaceutical Inc., 1580 East Hanley Boulevard, Tucson, Arizona 85737, USA. marcel.patek@aventis.com |
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Abstract: | A novel acid labile linker for solid-phase synthesis of substituted guanidines has been developed. Its synthetic utility is exemplified by high-yielding pyrazole displacement with structurally and electronically diverse sets of aliphatic and aromatic amines. The final cleavage is achieved by treatment with 95:5 trifluoroacetic acid/water for 1 h. The corresponding guanidines were obtained in high purity (80-95%) and good isolated yields (50-95%). The scope and limitations of this linker were further demonstrated by the solid-phase synthesis of an 880-member library of individual trisubstituted arylguanidines employing pyrazole displacement with a set of 11 anilines and two subsequent Mitsunobu N-alkylations with sets of 10 and 8 alcohols, respectively. |
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