Paper
SYNTHESIS OF 3-METHYLISOXAZOLE- 5-CARBOXAMIDES AND 5-[(1H-PYRAZOL-1-YL)CARBONYL]- 3-METHYLISOXAZOLES
Published Jan 1, 2002 · M. Martins, Marcelo Neto, A. Sinhorin
Synthetic Communications
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Abstract
ABSTRACT The one-pot synthesis of six 3-methylisoxazole-5-carboxamides 2 [where the N-substituents are R1 = H, Me and R2 = Ph, CH2Ph, n-Bu, C(CH3)2Et, 3-methylisoxazol-5-yl] and twelve 5-[(1H-pyrazol-1-yl)carbonyl]-3-methyl isoxazoles 3 and 4 [where the pyrazole substituents are R3 (C5/C3) = CO2Et, CF3 and R5 (C3/C5) = H, Me, Et, Ph] from the 3-methyl isoxazole-5-carboxylic acid, thionyl chloride and the corresponding amine or pyrazole is reported. In the synthesis of 5-[(1H-pyrazol-1-yl)carbonyl]-3-methylisoxazoles we obtained a mixture of 1,3- and 1,5-isomers 3 and 4 in variable ratios, i.e., the substituent R3 (CO2Et and CF3) are present in position 3 or 5 on the pyrazole ring.
This study presents a one-pot synthesis of 3-methylisoxazole-5-carboxamides and 5-[(1H-pyrazol-1-yl)carbonyl]-3-methyl isoxazoles, resulting in a mixture of 1,3- and 1,5-isomers in variable
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