280576-51-4

Upstream product

• 627-37-2 N-methyl-N-allylamine 
• 280576-49-0 2-chloro-5-methoxy-1-(4-methylphenyl)-1H-3-pyrrolcarbaldehyde 
• 280576-45-6 5-methoxy-1-(4-methylphenyl)-2,3-dihydro-1H-2-pyrrolone 

Downstream Products

• 823197-95-1 N'-[[2-[allyl(methyl)amino]-5-methoxy-1-(4-methylphenyl)-1H-pyrrol-3-yl]methylene]-4-methylbenzenesulfohydrazide 
• 280576-56-9 2-[allyl(methyl)amino]-5-methoxy-1-(4-methylphenyl)-1H-3-pyrrolcarbaldehydeoxime 

Relevant academic research and scientific papers

1-Aryl-2-chloro-5-methoxy-1H-3-pyrrolecarbaldehyde as synthons for fused heterocycles: synthesis of pyrazolo[3,4-d]pyrrolo[2,3-b]pyridine derivatives

Pyrazolo[3,4-d]pyrrolo[2,3-b]pyridine derivatives (6a-f) were obtained by oxidation of tosylhydrazones of 2-allylamino-5-methoxypyrrole-3-carbaldehydes (3a-f) with lead tetraacetate. The nitrilimine intermediates (5a-f) underwent intramolecular 1,3-dipolar cycloaddition to yield the tricyclic heterocycles 6a-f in good yields.

1-Aryl-5-methoxy-pyrrolones as synthons for 1,3-dipolar cycloadditions

A general method is described to convert the title compound into more complex nitrogen heterocyclic systems in a short and attractive pathway. Spiroisoxazolidine 6 was obtained from the reaction of nitrone 3 with ethyl vinyl ether. Chloroformylation of pyrrolone 2 gave 1-aryl-2-chloro-5-methoxy- pyrrol-3-carbaldehyde 4. Substitution of chlorine atom with unsaturated nucleophiles 8a,b and then modifying the aldehyde function into 1,3-dipoles 10 and 14 furnished tricyclic heterocycles 11, 12 and 15 via intramolecular 1,3-dipolar cycloaddition reaction. (C) 2000 Elsevier Science Ltd.