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Properties and Reactions of Substituted 1,2‐Thiazetidine 1,1‐Dioxides: Synthesis of N ‐Substituted 4,4‐dimethyl‐1,2‐thiazetidin‐3‐one 1,1‐dioxides, and a new base‐catalyzed rearrangement to thiazolidin‐4‐one 1,1‐dioxides
Author(s) -
Glasl Dietmar,
Otto HansHartwig,
Rihs Grety
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800305
Subject(s) - chemistry , alkylation , solvolysis , sulfonate , ring (chemistry) , base (topology) , medicinal chemistry , crystal structure , catalysis , stereochemistry , organic chemistry , sodium , hydrolysis , mathematical analysis , mathematics
Alkylation of 3‐oxo‐1,2‐thiazetidine 1,1‐dioxide 2 yields the N ‐alkylated 3‐oxo‐β‐sultams 3a‐i . Solvolysis with NaOH or NH 3 selectively opens the NS bond forming the sulfonate carboxamides 4 and the sulfonamidocarboxamides 7 , respectively. Furthermore, the hitherto unknown compounds of type 5 are prepared, representing a strained four‐membered ring with a diacylated, sulfonated N‐atom. Depending upon the reaction conditions, 3b‐d and 3g are rearranged by base‐catalyzed reactions into the substituted 4‐oxothiazolidine 1,1‐dioxides 9 or 10. Structures are elucidated by spectroscopic methods, established by crystal‐structure analyses, and a possible way of formation is proposed. Furthermore, some side reactions and transformations are reported.