Patent ID: 6197967
Filing Date: 2001-03-06
Classification: C07F

Abstract:
Process for the preparation of para-oxadiazolylphenylboronic acid of the formula (I) ##STR19##in which R.sup.1 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -alkynyl, C.sub.1 -C.sub.12 -alkoxy, alkoxy-(C.sub.1 -C.sub.12 -alkyl), alkoxy-(C.sub.2 -C.sub.12 -alkenyl), alkoxy-(C.sub.2 -C.sub.12 -alkynyl), acyloxy-(C.sub.1 -C.sub.12 -alkyl), acyloxy-(C.sub.2 -C.sub.12 -alkenyl), acyloxy-(C.sub.2 -C.sub.12 -alkynyl), aryl, heteroaryl, OH, SH, F, Cl, Br, I or NR'R"", where R' and R"", independently of one another, are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl or aryl, R.sup.2 to R.sup.5, independently of one another, are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -alkynyl, C.sub.3 -C.sub.12 -cycloalkyl, (C.sub.1 -C.sub.12 -)-alkoxy, (C.sub.1 -C.sub.12)-acyloxy, O-phenyl, O-benzyl, aryl, heteroaryl, hydroxyl, fluorine, chlorine, bromine, iodine, nitro, CN, SO.sub.2 R or SOR, where R is hydrogen, C.sub.1 -C.sub.4 -alkyl, aryl, chlorine or fluorine, or are NH.sub.2, N(alkyl).sub.2, N[Si(C.sub.1 -C.sub.4 -alkyl).sub.3].sub.2, CF.sub.3, CCl.sub.3, COO-(C.sub.1 -C.sub.12 -alkyl), CO-(C.sub.1 -C.sub.12 -alkyl), CO-phenyl, COO-phenyl, CHCHCOO-(C.sub.1 -C.sub.2 -alkyl), PO-phenyl.sub.2, PO-(C.sub.1 -C.sub.8 -alkyl).sub.2 or PO.sub.3 (C.sub.1 -C.sub.8 -alkyl).sub.2, or R.sup.2 and R.sup.3, R.sup.4 and R.sup.5, or both, together form an aliphatic or aromatic ring, whereina compound of the formula (V) ##STR20##in which Z.sup.5 is --COOH;is reacted with a compound of the formula (X) ##STR21##to give the compound of the formula (I') ##STR22##in which Z.sup.1 is ##STR23##and the compound of the formula (I') is hydrolyzed to give the compound of the formula (I),or the compound of the formula (V) is firstly reacted with hydrazine to give a compound of the formula (II) ##STR24##in which Z.sup.2 is --CONHNH.sub.2, andthe compound of the formula (II) is cyclized and hydrolyzed;where Q.sup.1 and Q.sup.2 are each a radical of the formula --O-(C.sub.1 -C.sub.12)-alkyl, --O-(C.sub.2 -C.sub.12)-alkenyl, --O-(C.sub.2 -C.sub.12)-alkynyl, --O-aryl, --O-alkylaryl or --O-Si(C.sub.1 -C.sub.4 -alkyl).sub.3 ; or Q.sup.1, Q.sup.2 and the adjacent boron atom form a cyclic boronic ester with the following alcohols: (C.sub.3 -C.sub.12)cycloalkane-1,2-diol, (C.sub.5 -C.sub.12)-cycloalkene-1,2-diol, (C.sub.5 -C.sub.12)-cycloalkane-1,3-diol, (C.sub.5 -C.sub.12)-cycloalkene-1,3-diol or with alcohols of the formulae (Ia) to (If) ##STR25##in which R.sub.1 a to R.sub.8 a, independently of one another, are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 -hydroxyalkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -alkynyl, C.sub.3 -C.sub.12 -cycloalkyl, (C.sub.1 -C.sub.12)-alkoxy, (C.sub.1 -C.sub.12)-acyloxy, O-phenyl, O-benzyl, aryl, heteroaryl, fluorine, chlorine, bromine, iodine, NO.sub.2, CN, SO.sub.2 R, SOR, where R is as defined above, or are NH.sub.2, N(alkyl).sub.2, N[Si(C.sub.1 -C.sub.4 -alkyl).sub.3 ].sub.2, CF.sub.3, CCl.sub.3, CBr.sub.3, COO-(C.sub.1 -C.sub.12 -alkyl), CO-(C.sub.1 -C.sub.12 -alkyl), CO-phenyl, COO-phenyl, CHCHCOO-(C.sub.1 -C.sub.2 -alkyl), PO-phenyl.sub.2, PO-(C.sub.1 -C.sub.8 -alkyl).sub.2 or PO.sub.3 (C.sub.1 -C.sub.8 -alkyl).sub.2, or two adjacent radicals R.sub.1 a to R.sub.8 a together form an aliphatic or aromatic ring, and in which n is an integer from 2 to 12, or in which Q.sup.1 and Q.sup.2 together form a divalent radical of the formula (Ig) ##STR26##in which all radicals Z, in each case correspondingly, have one of the meanings of Z.sup.1 to Z.sup.5.