3,5-disubstituerade tetrahydrofuran-2-oner

摘要

3,5-Di:substd. tetrahydrofuran-2-ones (I) and their salts are new: R1 = opt. esterified COOH; hydroxymethyl; or formyl; R2, R4 = aliphatic, cycloaliphatic-aliphatic, araliphatic or heteroaryl-aliphatic gp.; R3 = N3; or NH2 opt. substd. by an aliphatic or araliphatic gp. and/or by an amino protecting gp. Certain starting materials and intermediates are also claimed. Further claimed is the conversion of (I) into aryl-substd. hydroxylated amino-alkanoic acid amides (II) by: (i) condensing (I) where R1 = CHO (obtd. as required from (I) where R1 = opt. esterified COOH by redn. or from (I) where R1 = CHOH by dehydrogenation) with a Grignard reagent (a); (ii) protecting the OH gp. in the resulting tertiary alcohol (b); (iii) reacting the protected alcohol (c) obtd. with an amine (d); and (iv) catalytically hydrogenating the prod. obtd. Ra = aromatic or heteroaromatic gp.; Rb = aliphatic, cycloaliphatic or heteroaromatic-aliphatic substd. amino; R = protecting gp.; R30 = amino mono- or di-substd. by lower alkyl or mono-substd. by lower alkanoyl; Q = H or OH.