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A convenient synthesis of the novel 5 H ‐thieno[2,3‐ e ]‐4,1,2‐oxathiazepine ring system via an alkoxycarbenium ion intermediate
Author(s) -
Dantanarayana Anura P.,
Dupre Brian,
May Jesse A.,
Lynch Vincent M.
Publication year - 1999
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.5570360111
Subject(s) - chemistry , ring (chemistry) , anhydrous , hydroxymethyl , carbonic anhydrase , stereochemistry , sulfonamide , molecule , medicinal chemistry , carbonic anhydrase ii , combinatorial chemistry , organic chemistry , enzyme
3‐(Methoxymethoxymethyl)‐2‐thiophenesulfonamides and 3‐hydroxymethyl‐ N ‐methoxymethyl‐2‐thiophenesulfonamides have been shown to undergo cyclization when treated under anhydrous acidic conditions to provide the novel 2,3‐dihydro‐5 H ‐thieno[2,3‐ e ]‐4,1,2‐oxathiazepine ring system. Incorporation of a primary sulfonamide group into position seven of the molecule provided compounds which inhibit human carbonic anhydrase II.