A practical synthesis of bicyclic sultams with a pyramidal bridgehead nitrogen atom and a sulfur atom in the apex position has been elaborated. Compounds with 1-azathiabicyclo[2.2.1]heptane (12a), -bicyclo[3.2.1]octane (12b, 12d), and -bicyclo[3.3.1]nonane (13b) skeletons were obtained by direct twofold inter/intramolecular alkylation of corresponding monocyclic sultams 9 and 10 with α,ω-dihalides 11 in

N- (2,(methoxycarbonyl)methanesulfanilides upon treatment with potassium carbonate in DMF furnish methyl 3-aryl-2,2-dioxo-2-thia-3-azabicyclo[n.1.0]alkane-1-carboxylates in yields ranging from 54 to 84 % (10 examples). The starting materials were obtained by sulfonylation of N-alkenylanilines with methyl (chlorosulfonyl)acetate and subsequent bromination. For the N-alkenylanilines (10 examples, 60-77 % yield) an

A wide range of five‐ and six‐membered sultams bearing an α‐ethoxycarbonyl‐α‐methyl substituent or an α‐aryl group (17 examples) were synthesized by the cyclodialkylation of α‐substituted methanesulfonanilides with α,ω‐dihaloalkanes in the presence of K2CO3 or under phase‐transfer catalysis (PTC) conditions. Upon treatment with K2CO3 in N,N‐dimethylformamide (DMF) or NaH in dimethyl sulfoxide (DMSO), N‐(2,3‐dibromopropyl)‐α‐toluenesulfonanilides furnished different 1,3‐diaryl‐2‐thia‐3‐azabicyclo[3.1.0]hexane 2,2‐dioxides in good to excellent yields (51–88 %, 16 examples). The 4‐methoxyphenyl (PMP) group was easily removed from the sultam nitrogen atom by treatment of the corresponding bicyclic sultams with cerium(IV) ammonium nitrate in acetonitrile (71–84 % yield, 6 examples).

Thiazole derivatives R 0260 Facile Access to Bicyclic Sultams with Methyl 1-Sulfonylcyclopropane-1-carboxylate Moieties. -(RASSADIN, V. A.; TOMASHEVSKIY, A. A.; SOKOLOV*, V. V.; RINGE, A.; MAGULL, J.; DE MEIJERE, A.; Eur.

The present new method constitutes a simple and efficient route to thiazine and thiazole derivatives.