133901-59-4

Upstream product

• 120780-17-8 3,4-Dimethyl-2-p-tolyl-2λ⁴-benzo[c][1,2]thiazine 2-oxide 
• 57772-51-7 2-Amino-α-ethyl-α-methyl-benzylalkohol 
• 615-36-1 2-bromoaniline 
• 551-93-9 2-aminoacetophenone 

Downstream Products

• 113290-51-0 (Z)-2-(2-methoxycarbonylaminophenyl)but-2-ene 
• 113290-51-0 (E)-2-(2-methoxycarbonylaminophenyl)but-2-ene 
• 17336-90-2 3,4-dimethylquinolin-2(1H)-one 
• 113290-61-2 (Z)-1,4-diacetoxy-2-(2-phthalimidophenyl)but-2-ene 
• 113290-60-1 (E)-1,4-diacetoxy-2-(2-phthalimidophenyl)but-2-ene 
• 113290-63-4 (Z)-2-(2-phthalimidophenyl)but-2-ene-1,4-diol 
• 113290-62-3 (E)-2-(2-phthalimidophenyl)but-2-ene-1,4-diol 
• 113318-88-0 (Z)-1,4-bibromo-2-(2-methoxycarbonylaminophenyl)but-2-ene 
• 113290-53-2 (E)-1,4-bibromo-2-(2-methoxycarbonylaminophenyl)but-2-ene 
• 113290-65-6 (Z)-2-(2-aminophenyl)but-2-ene-1,4-diol 
• 113290-58-7 1,4-dibromo-2-(2-phthalimidophenyl)but-2-ene 
• 113318-87-9 (E)-1,1,4-tribromo-2-(2-methoxycarbonylaminophenyl)but-2-ene 
• 138386-79-5 (3,4-Dimethyl-quinolin-2-yl)-(4-methoxy-phenyl)-amine 
• 138386-57-9 C₂₈H₂₆NP 

Relevant academic research and scientific papers

A general, regioselective synthesis of 2-alkenylanilines

Reduction of selected 2,1-benzothiazines with sodium amalgam leads to the formation of 2-alkenylanilines in high yield. The benzothiazines are readily available from the reaction of N-phenyl-S-(p-tolyl)sulfonimidoyl chloride with alkynes in the presence of aluminum chloride. The sulfonimidoyl chloride is derived from aniline, and the process described herein thus constitutes a high-yielding, regioselective functionalization of aniline.

Exploiting Iminoquinones as Electrophilic at Nitrogen "n+" Synthons for C-N Bond Construction

New methods for C-N bond construction exploiting the N-centered electrophilic character of iminoquinones are reported. Iminoquinones, generated in situ via the condensation of o-vinylanilines with benzoquinones, undergo acid-catalyzed cyclization to afford N-arylindoles in excellent yields. Under similar reaction conditions, homoallylic amines react analogously to afford N-arylpyrroles. Additionally, organometallic nucleophiles are shown to add to the nitrogen atom of N-alkyliminoquinones to provide amine products. Finally, iminoquinones are shown to be competent electrophiles for copper-catalyzed hydroamination.

Acyliminium ion-olefin cyclization leading to isoindolo[2,1-a]quinoline derivatives

Isoindolo[2,1-a]quinolines 10, 11, 12 were synthesized from hydroxylactams 8 or 9 via an N-acyliminium ion-π-olefin nucleophile cyclization reaction.