TY - JOUR
T1 - Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones
AU - Rebollar, Araceli
AU - Bautista, Rafael
AU - Gutiérrez, Rsuini U.
AU - Espinoza-Hicks, Carlos
AU - Mendieta, Aarón
AU - Zárate-Zárate, Daniel
AU - Martínez-Mora, Eder I.
AU - Labarrios-Morán, Ehecatl M.
AU - Vázquez, Miguel A.
AU - Delgado, Francisco
AU - Tamariz, Joaquín
N1 - Publisher Copyright:
© 2022 Sociedade Brasileira de Quimica. All rights reserved.
PY - 2022
Y1 - 2022
N2 - The hydrogenation of α-oximinoketones in methanol/HCl afforded α-aminoketones, which were applied without purification to the synthesis of 4-imidazolin-2-ones and 2-thiones, including chiral derivatives. The latter two series were obtained in high yields by a heteroannulation reaction of α-aminoketones with isocyanates and isothiocyanates, respectively. A double condensation of the α-aminoketones with two mol equivalents of the isocyanates produced a series of 4,5-dialkyl- N,3-diaryl-2-oxo-2,3-dihydro-1H-imidazole-1-carboxamides. With isothiocyanates, a single condensation reaction furnished a series of 4,5-dialkyl-1-aryl-1H-imidazole-2(3H)-thiones, which underwent alkylation with alkyl halides to form the corresponding 1-aryl-2-thioalkyl-1H-imidazoles in high yields.
AB - The hydrogenation of α-oximinoketones in methanol/HCl afforded α-aminoketones, which were applied without purification to the synthesis of 4-imidazolin-2-ones and 2-thiones, including chiral derivatives. The latter two series were obtained in high yields by a heteroannulation reaction of α-aminoketones with isocyanates and isothiocyanates, respectively. A double condensation of the α-aminoketones with two mol equivalents of the isocyanates produced a series of 4,5-dialkyl- N,3-diaryl-2-oxo-2,3-dihydro-1H-imidazole-1-carboxamides. With isothiocyanates, a single condensation reaction furnished a series of 4,5-dialkyl-1-aryl-1H-imidazole-2(3H)-thiones, which underwent alkylation with alkyl halides to form the corresponding 1-aryl-2-thioalkyl-1H-imidazoles in high yields.
KW - 4-imidazolin-2-ones
KW - 4-imidazolin-2-thiones
KW - heteroannulation
KW - α-aminoketones
KW - α-oximinoketones
UR - http://www.scopus.com/inward/record.url?scp=85127977973&partnerID=8YFLogxK
U2 - 10.21577/0103-5053.20210120
DO - 10.21577/0103-5053.20210120
M3 - Artículo
AN - SCOPUS:85127977973
SN - 0103-5053
VL - 33
SP - 13
EP - 27
JO - Journal of the Brazilian Chemical Society
JF - Journal of the Brazilian Chemical Society
IS - 1
ER -