Efficient Synthesis of Rhodanine-Based Amides via Passerini Reaction using Tetramethylguanidine-Functionalized Silica Nanoparticles as Reusable Catalyst

Baharfar, Robabeh; Azimi, Razieh; Barzegar, Sheida; Mohseni, Mojtaba

doi:10.5935/0103-5053.20150108

Acessibilidade / Reportar erro

Brasil

Journal of the Brazilian Chemical Society

Español English

Brasil

Español English

sumário « anterior atual seguinte »

Sumário

Articles • J. Braz. Chem. Soc. 26 (7) • July 2015 • https://doi.org/10.5935/0103-5053.20150108 copy

Efficient Synthesis of Rhodanine-Based Amides via Passerini Reaction using Tetramethylguanidine-Functionalized Silica Nanoparticles as Reusable Catalyst

Authorship SCIMAGO INSTITUTIONS RANKINGS

Novel rhodanine-based amide derivatives were prepared in good yields via Passerini reaction of rhodanine-N-acetic acid with aromatic aldehydes and tert-butyl isocyanide in the presence of tetramethylguanidine immobilized on silica nanoparticles (TMG-SiO₂ NPs) as a heterogeneous base catalyst. The synthesized compounds were evaluated for their antibacterial effects against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis.

Keywords:
Passerini reaction; rhodanine-N-acetic acid; tetramethylguanidine; heterogeneous catalysis; antibacterial agents

entry	Catalyst / mol%	Solvent	Temperature / ºC	time / h	Yield^a a Yield refer to isolated products. / %
1	−	THF	70	24	trace
2	SiO₂ NPs / 0.3 g	THF	70	24	trace
3	TiO₂ NPs / 15	THF	70	24	trace
4	MgO NPs / 15	THF	70	24	trace
5	TMG / 15	THF	70	24	trace
6	DABCO / 15	THF	70	24	trace
7	SBA-15-DABCO / 15	THF	70	24	20
8	DBU- SiO₂ NPs / 15	THF	70	24	30
9	TMG-SiO₂ NPs / 15	THF	70	10	81
10	TMG-SiO₂ NPs / 20	THF	70	10	80
11	TMG-SiO₂ NPs / 10	THF	70	10	80
12	TMG-SiO₂ NPs / 5	THF	70	24	30
13	TMG-SiO₂ NPs / 10	CH₂Cl₂	40	24	35
14	TMG-SiO₂ NPs / 10	EtOH	80	24	−
15	TMG-SiO₂ NPs / 10	H₂O	100	24	−
16	TMG-SiO₂ NPs / 10	THF	40	24	45
17	TMG-SiO₂ NPs / 10	THF	25	24	trace

Compound	E. coli / mm	P. aeruginosa / mm	S. aureus / mm	B. subtilis / mm
4a ^a a Concentration of compounds 4a-4j: 20 mg mL-1;.	10.5 ± 0.7	9.5 ± 0.7	11.5 ± 0.7	9.5 ± 0.7
4b	NE^b b no effect	NE	9.5 ± 0.7	8.5 ± 0.7
4c	NE	NE	NE	NE
4d	NE	NE	8.5 ± 0.7	12.5 ± 0.7
4e	9.5 ± 0.7	NE	NE	7.5 ± 0.7
4f	NE	NE	NE	8.0 ± 0.1
4g	8.5 ± 0.7	NE	NE	NE
4h	12.0 ± 1.4	NE	16.0 ± 1.4	15.5 ± 0.7
4i	NE	NE	NE	NE
4j	NE	NE	NE	NE
Gentamicin (10 µg / disc)	19.6 ± 1.1	15.6 ± 0.5	20.3 ± 1.5	26.0 ± 1.7
Chloramphenicol (30 µg / disc)	20.7 ± 1.5	NE	21.7 ± 0.6	22.3 ± 1.2
DMSO	NE	NE	NE	NE

Sociedade Brasileira de Química Instituto de Química - UNICAMP, Caixa Postal 6154, 13083-970 Campinas SP - Brazil, Tel./FAX.: +55 19 3521-3151 - São Paulo - SP - Brazil
E-mail: office@jbcs.sbq.org.br

Acompanhe os números deste periódico no seu leitor de RSS

[1] *e-mail: baharfar@umz.ac.ir