TY - JOUR
T1 - Design and synthesis of some carbamazepine derivatives using several strategies
AU - Lauro, Figueroa Valverde
AU - Francisco, Díaz Cedillo
AU - Marcela, Rosas Nexticapa
AU - Guadalupe, Maldonado Velázquez
AU - Elodia, Maldonado García Cervera
AU - Eduardo, Maldonado Pool Gómez
AU - Horacio, Maldonado Jarquín Barberena
AU - María, Maldonado López Ramos
AU - Fernanda, Maldonado Rodríguez Hurtado
AU - Marissa, Maldonado Chan Salvador
N1 - Publisher Copyright:
© 2015 Bentham Science Publishers.
PY - 2015
Y1 - 2015
N2 - In this study, is reported a straightforward route is reported for the synthesis of a series of carbamazepine derivatives using some strategies. The first stage was achieved by the reaction of carbamazepine with thiourea in the presence of pyridine to form the compound 3-(5H-dibenzo[b,f]azepin-5-yl)-2,5-dihydro-1,2,4-thiadiazol-5-amine (3). After 3 was made reacting with chloroacetyl chloride using triethylamine as catalyst to synthesis of a propanamide derivative (4). The following stage a carboxamide derivative (5) was synthesized by the reaction of 4 with benzaldehyde in basic medium. The fourth stage was achieved by the reaction of carbamazepine with ethylenediamine in presence of formaldehyde to form a new carboxamide derivative (7). Then, the compound 7 was made reacting with 2-hydroxy-1-naphthaldehyde using boric acid as catalyst to synthesis of a carbamazepine derivative (8). Finally, 8 was made reacting with 3,5-dintrobenzoic acid in the presence of dimetyhyl sulfoxide at mild conditions to form a new carbamazepine derivative 9. The structure of the compounds obtained was confirmed by elemental analysis, spectroscopy and spectrometry data. The proposed method offers some advantages such as simple procedure, low cost, and ease of workup.
AB - In this study, is reported a straightforward route is reported for the synthesis of a series of carbamazepine derivatives using some strategies. The first stage was achieved by the reaction of carbamazepine with thiourea in the presence of pyridine to form the compound 3-(5H-dibenzo[b,f]azepin-5-yl)-2,5-dihydro-1,2,4-thiadiazol-5-amine (3). After 3 was made reacting with chloroacetyl chloride using triethylamine as catalyst to synthesis of a propanamide derivative (4). The following stage a carboxamide derivative (5) was synthesized by the reaction of 4 with benzaldehyde in basic medium. The fourth stage was achieved by the reaction of carbamazepine with ethylenediamine in presence of formaldehyde to form a new carboxamide derivative (7). Then, the compound 7 was made reacting with 2-hydroxy-1-naphthaldehyde using boric acid as catalyst to synthesis of a carbamazepine derivative (8). Finally, 8 was made reacting with 3,5-dintrobenzoic acid in the presence of dimetyhyl sulfoxide at mild conditions to form a new carbamazepine derivative 9. The structure of the compounds obtained was confirmed by elemental analysis, spectroscopy and spectrometry data. The proposed method offers some advantages such as simple procedure, low cost, and ease of workup.
KW - Boric acid
KW - Carbamazepine
KW - Synthesis
KW - Thiourea
UR - http://www.scopus.com/inward/record.url?scp=84951777512&partnerID=8YFLogxK
U2 - 10.2174/1570178612666150331205124
DO - 10.2174/1570178612666150331205124
M3 - Artículo
SN - 1570-1786
VL - 12
SP - 394
EP - 401
JO - Letters in Organic Chemistry
JF - Letters in Organic Chemistry
IS - 6
ER -