1,2-Thiazetidine 1,1-dioxides synthesis

Mueller, M. and Otto, H. H., Properties and reactions of substituted 1,2-thiazetidine 1,1-dioxides Synthesis of N-aminoalkylated 1,2-thiazetidine 1,1-dioxides, Arc/i. Pharm, 322, 515, 1989. 

Four-membered ring adducts from 2n + 2n cycloaddition of keten-imines to sulfur dioxide. Isolation of l,2-thiazetidin-3-one 1-oxides. jS-Sultames. Simple method for synthesis of substituted 1,2-thia-zetidin 1,1-dioxide. ... 

The synthesis of 3-alkyl-substituted 1,2-thiazetidine 1,1-dioxides starts by transformation of the amino acids L-Val, L-Leu, L-Ile, and L-Phe into amino alcohols. These ate converted via the bromides to the corresponding thiols 161. Immediate oxidative chlorination affords either sulfonyl chloride hydrochlorides or sulfonic acids 162 which are transformed into the parent /3-sultams 163 <2004HCA90>. Similarly, L-cystine derivatives 164 have also been transformed into the parent /3-sultams 165 by oxidative chlorination followed by cyclization (Scheme 50) C1997LA1261, 2004HCA90>. 

A convenient synthesis of benzo[z]-l,2-thiazetidine 1,1-dioxides (1,2-benzosultams) 191 is based on a demethylative intramolecular cyclization of the sulfonic acid 190 (Scheme 116) <1998JOC2348, CHEC-III(2.15.8.2.2)755>. 

Intramolecular cyclization of 2-aminoethanesulfonyl halides gives 1,2-thiazetidine 1,1-dioxides ((3 sultams), as exemplified in the synthesis of 429. ° Treatment of 2-halosulfonylethanoyl halides with ammonia or primary amines yields 1,2-thiazetidin-3-one 1,1-dioxides, which are mixed sulfonic-carboxylic imides 430. A 3-imino derivative has also been obtained. ... 

Because of their structural similarity to the fi-lactams, the solid-phase synthesis of 3-sultams (1,2-thiazetidine-l,1-dioxides) is of relevance. However, in spite of their structural analogy to the fi-lactams, very little is known about the biological activity of P-sultams. Thus far, the P-sultams examined have shown disappointingly weak P-lactamase inhibition activity [49], although by using combinatorial technologies... 

The synthesis of A -substituted 4,4-dimethyl-l,2-thiazetidin-3-one 1,1-dioxides 42 (R = CH2R ) and a new ba.se catalysed rearrangement of this compound to thiazolidin-4-one I, I-dioxides 43 is reported <97HCA671>. 

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