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Synthese von [1,1,3‐Trioxo‐1,2‐benzisothiazol‐2(3 H )‐yl]keten‐ S , S ‐acetalen und deren Hydrazinolyse
Author(s) -
Dölling Wolfgang,
Herrmann Cornelia,
Augustin Manfred
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001170
Subject(s) - chemistry , ketene , propiophenone , hydrazine (antidepressant) , hydrate , medicinal chemistry , methylene , sodium hydride , alkylation , hydrazone , organic chemistry , ketone , catalysis , chromatography
Synthesis of [1,1,3‐Trioxo‐1,2‐benzisothiazol‐2(3 H )‐yl]ketene S , S ‐Acetals and Their Reaction with Hydrazine Hydrate The previously unknown ketene S , S ‐acetals 2 , 3 , and 4 are prepared by dithiocarboxylation reaction of methylene‐active saccharin derivatives 1 in the presence of sodium hydride/carbon disulfide in dry DMF followed by alkylation. Compounds 2a , 3a , and 4a are treated with hydrazine hydrate (85%) to give 2‐hydrazono‐3,3‐bis(methylthio)propiophenone ( 6a ) and methyl or ethyl pyruvate 6b or 6c , respectively.