Synthesis and mass spectral fragmentation patterns
of some nitrogen heterocycles with antimicrobial
M. H. Sherif
Received: 16 November 2012 / Accepted: 27 December 2012 / Published online: 13 January 2013
Ó Springer Science+Business Media Dordrecht 2013
Abstract 5-(P-tolyl)-2-[(3-bromo-4-methoxy benzylidene) hydrazino]-thiazole 3,
3-[(3-bromo-4-mehtoxy benzylidine) amino]-2-thiohydantion 5, and 4,6-disubsti-
tuted-3-[(3-bromo-4-methoxybenzyliden) amino]-2-thioxo pyrimidines 10 have
been prepared via cyclization of 3-bromo-4-methoxy benzaldehyde thiosemicar-
bazone 2 with 4-methyl phenacyl bromide, ethyl chloroacetate, and dicarbonyl
compounds in different conditions. Acetylation of 3 and 5 with acetic anhydride
gave the corresponding monoacetyl derivatives 4 and 6, while the acetylation of 5
with acetic anhydride in the presence of fused sodium acetate gave diacetyl
derivative 7. Condensation of compound 5 with benzaldehyde in the presence of
piperidine yielded the corresponding 3-substituted-5-benzylindene 2-thiohydation 8.
Acetylation of compound 8 with acetic anhydride gave the corresponding 1-acetyl-
3-substituted-5-benzylidene-2-thiohydantion 9. The mass spectral fragmentation
patterns of some prepared compounds are investigated in order to elucidate the
structure of the synthesized nitrogen heterocycles.
Keywords Mass spectroscopy Á Nitrogen heterocycles Á Antimicrobial activity
Various substituted nitrogen heterocyclic compounds have recently achieved
signiﬁcant importance because of their diverse pharmacological properties [1–6].
These include analgesic, antiasthmatic, diuretic, antihypertensive, anticholinergic,
and anti-inﬂammatory properties. The hydration is an antimicrobial drug for the
treatment of urinary tract infections, while its analog Dantrolene represents a well-
known skeletal muscle relaxant.
M. H. Sherif (&)
Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt
e-mail: email@example.com; firstname.lastname@example.org
Res Chem Intermed (2014) 40:887–901