Premium
The synthesis and reactions of certain 3‐substituted‐2,1‐benzisothiazoles
Author(s) -
Albert Anthony H.,
O'Brien Darrrell E.,
Robins Roland K.
Publication year - 1978
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.5570150401
Subject(s) - chemistry , nucleophilic substitution , medicinal chemistry , ring (chemistry) , potassium , hydrogen peroxide , nitro , sulfide , hydrogen sulfide , nucleophile , organic chemistry , hydrogen chloride , catalysis , sulfur , alkyl
A new and general synthesis of 2,l‐benzisothiazolin‐3‐ones ( 2 ) is described from the corresponding isatoic anhydride ( 3 ) and potassium hydrogen sulfide which gives the thioanthranilic acid ( 4 ) which is readily oxadized and ring closed to 2 with hydrogen peroxide. Phosphorus oxy‐chloride converted 3‐hydroxy‐2,1‐benzisothiazole to 3‐chloro‐2,1‐benzisothiazole which gave a number of different 3‐substiluted 2,1‐benzisothiazolesby nucleophilic substitution of the 3‐chloro group. Rleetrophilie substitution of 1‐methyl‐2,1 ‐benzisothiazoIin‐3‐one ( 2i ) proceeded readily to give the corresponding 5‐bromo‐, 5‐nitro‐, and 5‐chlorosulfonyl‐1‐methyl‐2,1‐benzisothiazolin‐3‐one. This appears to be a good synthetic route to such 2,1‐benzisothiazole derivatives.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom