The preparation of N-(1H-pyrazol-3-yl)arylamides and 1H-pyrazol-3-amines from polylithiated C(α),N-thiosemicarbazones and C(α),N-semicarbazones
✍ Scribed by Charles F. Beam; Sharon E. Davis; Tracy L. Cordray; Kam W. Chan; Camille M. Kassis; Joanna G. Freeman Davis; G. Mark Latham; Tina S. Guion; Karen C. Hildebran; A. Cameron Church; Madlene U. Koller; Clyde R. Metz; William T. Pennington; Kevin L. Schey
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1997
- Tongue
- English
- Weight
- 531 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
C(α),N‐Thiosemicarbazones or C(α),N‐semicarbazones were polylithiated with excess lithium diiso‐propylamide, and the resulting cyclized intermediates were condensed with aromatic esters to afford N‐(1__H__‐pyrazol‐3‐yl)arylamides. The polylithiated intermediates were also quenched with aqueous acid to give 5‐substituted, 1__H__‐pyrazol‐3‐amines.
📜 SIMILAR VOLUMES
Select C(α),N-phenylhydrazones were dilithiated in excess lithium diisopropylamide followed by condensation with methyl 2-(aminosulfonyl)benzoate and acid cyclization to afford new pyrazol-benzenesulfonamides, 2-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamides.
## Abstract magnified image Select C(α), __N__‐carbo‐__tert‐__butoxyhydrazones were dilithiated with excess lithium diisopropylamide followed by condensation with methyl 2‐(aminosulfonyl)benzoate, acid cyclization, hydrolysis, and decarboxylation to afford new 2‐(1__H__‐pyrazol‐5‐yl)benzenesulfona