Laha, Joydev K.; Jethava, Krupal P.; Tummalapalli, K. S. Satyanarayana; Sharma, Sheetal published the artcile< Synthesis of mono-N-sulfonylimidazolidines by a 1,3-dipolar cycloaddition strategy, as an alternative to selective N-sulfonylation and their ring cleavage to afford 1,2-diamines>, Synthetic Route of 1524-40-9, the main research area is sulfonyl diamine preparation; monosulfonylimidazolidine preparation ring cleavage; azomethine ylide sulfonylimine dipolar cycloaddition; sulfamidate fused imidazolidine preparation; sulfonylketimine azomethine ylide dipolar cycloaddition.
Mono-N-sulfonylimidazolidines I [R1 = H, 4-Me, 4-MeO, 2-OEt, 2,4,6-Me3; R2 = Ts, SO2CH2Ph, 3-FC6H4SO2; R3 = H, 3-MeO, R4 = H, Me; X = bond, CHR4] were synthesized via 1,3-dipolar cycloaddition between nonstabilized azomethine ylides and N-sulfonylimines. The enhanced reactivity of N-sulfonylimines as dipolarophiles toward azomethine ylides largely eliminated possible Michael addition and favored 1,3-dipolar cycloaddition Sulfamidate fused imidazolidines II [R5 = H, Cl; Y = CH2, CH2CH2] were obtained via 1,3-dipolar cycloaddition between azomethine ylides and N-sulfonylketimine. Nucleophile-dependent ring cleavage of N-sulfonylimidazolidines I produced synthetically useful mono-N-sulfonyl-1,2-diamines III [R6 = H, Me, MeO; R7 = H, Me; R8 = Bn, 3-MeOC6H4CH2]. Ring cleavage accompanied by CH2 extrusion, yielded N-[2-(Benzylamino)-1-(p-tolyl)ethyl]-4-methylbenzenesulfonamide III [R6 = Me; R7 = H; R8 = Bn], occurred on treatment with TBAF, whereas N-{2-[Benzyl(methyl)amino]-1-(4-methoxyphenyl)ethyl}-4-methylbenzenesulfonamide III [R6 = MeO; R7 = Me; R8 = Bn] and N-{2-[(3-Methoxybenzyl)(methyl)amino]-1-phenylethyl}-4-methylbenzenesulfonamide III [R6 = H; R7 = Me; R8 = 3-MeOC6H4CH2] were produced on treatment with LAH.
European Journal of Organic Chemistry published new progress about 1,3-Dipolar cycloaddition reaction. 1524-40-9 belongs to class amides-buliding-blocks, and the molecular formula is C6H6FNO2S, Synthetic Route of 1524-40-9.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics