Journal
HETEROCYCLIC COMMUNICATIONS
Volume 22, Issue 3, Pages 143-149Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1515/hc-2016-0002
Keywords
antimicrobial activity; antipyrine; Mannich reaction; microwave
Categories
Funding
- Karadeniz Technical University, BAP, Turkey [8663, 8623]
Ask authors/readers for more resources
N-Benzyl-N'-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) urea (1) was obtained from antipyrine. The reaction of 1 with ethyl bromoacetate produced the 1,3-oxazole derivative 2. Compounds 5a-c were obtained from antipyrine by three steps via intermediary of the ester 3 and hydrazide 4. The microwave supported cyclocondensation of 5a-c with 4-chlorophenacyl bromide and ethyl bromoacetate afforded the corresponding 1,3-thiazoles 6 or 1,3-thia(oxa) zolidines 7. The intramolecular cyclization of 5a-c in the presence of NaOH produced the corresponding triazoles 8a-c. The synthesis of the hybrid compound 9 containing a penicillin skeleton was carried out by the treatment of 8a with (+)-6-aminopenicillanic acid (6-apa) in the presence of formaldehyde. The structural assignments of new compounds were based on their elemental analysis and spectral (IR, H-1-NMR, C-13-NMR and LC-MS) data. All compounds except 1 and 7b show moderate antimicrobial activity.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available