SYNTHESIS AND TAUTOMERISM OF NEW 1-n-ALKYL-5-PYRAZOLONE DERIVATIVES
3-Phenyl-5-pyrazolone (1) is selectively alkylated at position 1 in 40% yield. The alkylated compound (2) is acylated (3) in 60% yield and nitrosated (4) in 80% yield. According to the spectroscopic data a N-H or O-H structure can be proposed for 1 in DMSO. The proton may be at N-2 or on the oxygen...
Guardado en:
| Autores principales: | , , , |
|---|---|
| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
1999
|
| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0366-16441999000300014 |
| Etiquetas: |
Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
|
| id |
oai:scielo:S0366-16441999000300014 |
|---|---|
| record_format |
dspace |
| spelling |
oai:scielo:S0366-164419990003000142000-10-13SYNTHESIS AND TAUTOMERISM OF NEW 1-n-ALKYL-5-PYRAZOLONE DERIVATIVESBELMAR,J.ALDERETE,J.PARRA,M.ZUÑIGA,C. Tautomerism alkylpyrazolones pyrazolones chelating pyrazolones synthesis 3-Phenyl-5-pyrazolone (1) is selectively alkylated at position 1 in 40% yield. The alkylated compound (2) is acylated (3) in 60% yield and nitrosated (4) in 80% yield. According to the spectroscopic data a N-H or O-H structure can be proposed for 1 in DMSO. The proton may be at N-2 or on the oxygen at C-5, respectively. The alkylated compound 2 exists as 5-pyrazolone in chloroform with a CH2 at C-4. In DMSO, 2 is a 5-hydroxypyrazole. For compound 3 in chloroform the structure corresponds to 4-acyl-5-hydroxypyrazole. For compound 4 in chloroform there is one tautomer with a 4-nitroso-5-hydroxypyrazole structure while in DMSO the same 4-nitroso-5-hydroxypyrazole (92%) and a 4-nitroso-5-pyrazolone (8%) tautomer can be foundinfo:eu-repo/semantics/openAccessSociedad Chilena de QuímicaBoletín de la Sociedad Chilena de Química v.44 n.3 19991999-09-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0366-16441999000300014en10.4067/S0366-16441999000300014 |
| institution |
Scielo Chile |
| collection |
Scielo Chile |
| language |
English |
| topic |
Tautomerism alkylpyrazolones pyrazolones chelating pyrazolones synthesis |
| spellingShingle |
Tautomerism alkylpyrazolones pyrazolones chelating pyrazolones synthesis BELMAR,J. ALDERETE,J. PARRA,M. ZUÑIGA,C. SYNTHESIS AND TAUTOMERISM OF NEW 1-n-ALKYL-5-PYRAZOLONE DERIVATIVES |
| description |
3-Phenyl-5-pyrazolone (1) is selectively alkylated at position 1 in 40% yield. The alkylated compound (2) is acylated (3) in 60% yield and nitrosated (4) in 80% yield. According to the spectroscopic data a N-H or O-H structure can be proposed for 1 in DMSO. The proton may be at N-2 or on the oxygen at C-5, respectively. The alkylated compound 2 exists as 5-pyrazolone in chloroform with a CH2 at C-4. In DMSO, 2 is a 5-hydroxypyrazole. For compound 3 in chloroform the structure corresponds to 4-acyl-5-hydroxypyrazole. For compound 4 in chloroform there is one tautomer with a 4-nitroso-5-hydroxypyrazole structure while in DMSO the same 4-nitroso-5-hydroxypyrazole (92%) and a 4-nitroso-5-pyrazolone (8%) tautomer can be found |
| author |
BELMAR,J. ALDERETE,J. PARRA,M. ZUÑIGA,C. |
| author_facet |
BELMAR,J. ALDERETE,J. PARRA,M. ZUÑIGA,C. |
| author_sort |
BELMAR,J. |
| title |
SYNTHESIS AND TAUTOMERISM OF NEW 1-n-ALKYL-5-PYRAZOLONE DERIVATIVES |
| title_short |
SYNTHESIS AND TAUTOMERISM OF NEW 1-n-ALKYL-5-PYRAZOLONE DERIVATIVES |
| title_full |
SYNTHESIS AND TAUTOMERISM OF NEW 1-n-ALKYL-5-PYRAZOLONE DERIVATIVES |
| title_fullStr |
SYNTHESIS AND TAUTOMERISM OF NEW 1-n-ALKYL-5-PYRAZOLONE DERIVATIVES |
| title_full_unstemmed |
SYNTHESIS AND TAUTOMERISM OF NEW 1-n-ALKYL-5-PYRAZOLONE DERIVATIVES |
| title_sort |
synthesis and tautomerism of new 1-n-alkyl-5-pyrazolone derivatives |
| publisher |
Sociedad Chilena de Química |
| publishDate |
1999 |
| url |
http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0366-16441999000300014 |
| work_keys_str_mv |
AT belmarj synthesisandtautomerismofnew1nalkyl5pyrazolonederivatives AT alderetej synthesisandtautomerismofnew1nalkyl5pyrazolonederivatives AT parram synthesisandtautomerismofnew1nalkyl5pyrazolonederivatives AT zunigac synthesisandtautomerismofnew1nalkyl5pyrazolonederivatives |
| _version_ |
1718438095700885504 |