DIRECTIONS OF REACTIONS OF 6-AMINO-, -ACETYLAMINO-, AND -BENZOYLAMINODEOXYVASICINONES WITH ALDEHYDES

6-Acetylamino- and -benzoylamino-9-arylidenedeoxyvasicinones were synthesized by reaction of 6-amino-(3), -acetylamino-(4), and -benzoylamino-(5) -deoxyvasicinones (DOV) with aromatic aldehydes and furfurol in glacial acetic acid. It was shown that the amino group of 6-aminodeoxyvasicinone underwent acylation upon reaction with aldehydes to form 6-acetylamino-DOV, which reacted with aldehydes to form 9-arylidene derivatives. Carrying out this condensation in toluene, o-xylene, and ethanol produced a mixture of condensation products at the 6-amino- and alpha-CH(2)-groups. It was found that condensation of 3 with 4-nitrobenzaldehyde in pyridine formed exclusively the Schiff bases. Methods for preparing 6-nitrodeoxyvasicinone and for its reduction were improved.