Helvetica Chimica Acta p. 671 - 683 (1997)
Update date:2022-08-03
Topics:
Glasl
Ribs
Otto
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 NH3 selectively opens the N-S 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.
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Doi:10.1039/b604073j
(2006)Doi:10.1021/om9702237
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(1997)Doi:10.1002/ejoc.200800213
(2008)Doi:10.1021/ja970502l
(1997)Doi:10.1016/S0960-894X(03)00102-1
(2003)