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Derivatives of 2‐oxo‐3(2 H )‐benzothiazolineacetonitrile and related compounds. I. Synthesis of N ‐hydroxy‐2‐oxo or thioxo‐3(2 H )‐benzothiazolineethanimidamide and related products
Author(s) -
D'Amico John J.,
Marvel John T.,
Bollinger Frederic G.
Publication year - 1988
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.5570250520
Subject(s) - acetonitriles , chemistry , hydroxylamine , medicinal chemistry , dehydration , organic chemistry , pentoxide , acetonitrile , biochemistry , vanadium
Abstract The following methods afforded the titled acetonitriles 1–5 in excellent yields: (1) the reaction of the appropriate 2‐benzothiazolinones with chloroacetonitrile under basic conditions and (2) the dehydration of the appropriate 2‐oxo‐3(2 H )‐benzothiazolineacetamides with phosphorus oxychloride or pentoxide. The reaction of the acetonitriles 1–5 and 2‐thioxo‐3(2 H )‐benzothiazolmeacetonitrile with hydroxylamine afforded the titled compounds 6–11 . Supporting nmr and mass spectral data are discussed.