1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH4 CO2 H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2′-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1H)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induced oxidative stress, α-glucosidase and DPP4 inhibition, showing potential application as anti-diabetics.

Marzullo P., Vasto S., Buscemi S., Pace A., Nuzzo D., Palumbo Piccionello A. (2021). Ammonium formate-Pd/C as a new reducing system for 1,2,4-oxadiazoles. Synthesis of guanidine derivatives and reductive rearrangement to quinazolin-4-ones with potential anti-diabetic activity. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22(22), 1-16 [10.3390/ijms222212301].

Ammonium formate-Pd/C as a new reducing system for 1,2,4-oxadiazoles. Synthesis of guanidine derivatives and reductive rearrangement to quinazolin-4-ones with potential anti-diabetic activity

Marzullo P.
Primo
Writing – Original Draft Preparation
;
Vasto S.
Secondo
Methodology
;
Buscemi S.
Formal Analysis
;
Pace A.
Validation
;
Nuzzo D.
Penultimo
Resources
;
Palumbo Piccionello A.
Ultimo
Conceptualization
2021-11-14

Abstract

1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH4 CO2 H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2′-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1H)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induced oxidative stress, α-glucosidase and DPP4 inhibition, showing potential application as anti-diabetics.
14-nov-2021
Marzullo P., Vasto S., Buscemi S., Pace A., Nuzzo D., Palumbo Piccionello A. (2021). Ammonium formate-Pd/C as a new reducing system for 1,2,4-oxadiazoles. Synthesis of guanidine derivatives and reductive rearrangement to quinazolin-4-ones with potential anti-diabetic activity. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22(22), 1-16 [10.3390/ijms222212301].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/527882
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