Synthesis and antifungal properties of benzylamines containing boronate esters

Addition of 3-H(2)NC(6)H(4)Bpin (pin = 1,2-O2C2Me4) to a series of aldehydes and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acetophenone afforded the corresponding benzylideneamines in moderate to high yields. Hydroboration of these imines with catecholborane (HBcat, cat = 1,2-O2C6H4) at room temperature gives, upon aqueous workup, the corresponding borylamines. An X-ray diffraction study was carried out on imine 1h derived from 9-anthraldehyde and 3-H(2)NC(6)H(4)Bpin. Crystals of 1h were triclinic, a = 9.6793(4) Angstrom, b = 10.7397(4) Angstrom, c = 11.5353(4) Angstrom, alpha = 105.1890(10)degrees, beta = 97.3030(10)degrees, gamma = 102.1480(10)degrees, Z = 2 with space group P(1) over bar and crystals of N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-methoxybenzylamine 2c were orthorhombic, a = 8.6612(4) Angstrom, b = 10.3794(4) Angstrom, c = 20.6033(9) Angstrom, Z = 4 with space group P2(1)2(1)2(1). Amines have been tested for their antifungal properties against Aspergillus niger and Aspergillus flavus.