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Synthesis and [3+2]cycloadditions of N-(trimethylsilylmethyl)isothioureas: a synthetic equivalent of novel 1,3-dipolar reagent, iminoazomethine ylid

✍ Scribed by Yoshinori Tominaga; Koichiro Ogata; Shinya Kohra; Makoto Hojo; Akira Hosomi

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
300 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

N-(Trrmethylsrlylmethyl)~sothzoureas, readdy prepared by ihe reaction of N-hs(methylthzo)methylenecyanamtde or -p-toluenesulfonamuie wrth (tr~methylstlylmethyl)amme, followed by N-alkylatzon. have been found to be a symhettc equrvalenr of zmznoazomethrne ylrd Treatment of these compounds wzth cesrum jluoruie zn the presence of reactrve heterodrpolarophrles such as carbonyl compoundr q$jorded 1,3-drpolar cycloa&iucts, 2-zmuwoxazolrdtner and 2-lmmothlazohdmnes, VIQ 1,3-elJmmatron of (methylthro

)trrmerhylskme 1,3-Dipoar cycload&tlon reachon IS one of the most unportant and mtereshng reaction to construct fivemembered nng heterocycles from a synthetic pomt of view *v3 Among these reacnons, azomethlne yhds are widely used for the preparahon of N-contammg five-membered heterocycles 2h-J,3 We have reported that tailormade alkyhdeneazomethme yhds can be generated by the 1,3-ehmmat~on reaction of N-(mmethyldyhnethyl)substituted ketene N,S-acetals promoted by fluonde Ion and that [3+2]cycloaddthons to a variety of dlpolaro-ph1les are achieved, glvmg N-contaming 2-alkyhdeneheterocycles 3 These ketene S,N-acetals consldered as a precursor of azomethme yhds are obtamed by the addihon-ehmlnatlon reachon of (tnmethyls~lylmethyl)amme with the correspondmg ketene dlthloacetals 4,5 Dunng the course of our studies on the potenhal use of new s&on-based 1,3-dlpolar synthons by a 1,3-ehmmat~on reaction ,s-h13 it has been observed that N-(alylmethyl)-substituted isothloureas (3 and 4) are a useful precursor to previously unknown and otherwise maccesslble mxnoazomethme yhds (5) (Scheme 1) We now descnbe the preparanon and reachons of 3 and 4 SMe CH, ,+&

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