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The preparation of N‐(1 H ‐pyrazol‐3‐yl)arylamides and 1 H ‐pyrazol‐3‐amines from polylithiated C(α), N ‐thiosemicarbazones and C(α), N ‐semicarbazones
Author(s) -
Beam Charles F.,
Davis Sharon E.,
Cordray Tracy L.,
Chan Kam W.,
Kassis Camille M.,
Davis Joanna G. Freeman,
Latham G. Mark,
Guion Tina S.,
Hildebran Karen C.,
Church A. Cameron,
Koller Madlene U.,
Metz Clyde R.,
Pennington William T.,
Schey Kevin L.
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340527
Subject(s) - chemistry , lithium (medication) , aqueous solution , medicinal chemistry , stereochemistry , organic chemistry , medicine , endocrinology
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.