87281-44-5

Upstream product

• 50-00-0 formaldehyd 
• 922-67-8 propynoic acid methyl ester 
• 4043-87-2 pipecolic Acid 
• 87281-40-1 1-Trimethylsilanylmethyl-piperidine-2-thione 

Downstream Products

• 16959-59-4 5,6,7,8-tetrahydroindolizine-2-carboxylic acid 
• 1433820-64-4 2-[5-fluoro-2-(hydroxymethyl)-3-[6-[4-[4-(oxetan-3-yl)piperazin-1-yl]anilino]-9H-purin-2-yl]phenyl]-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-one 
• 1433824-32-8 4-fluoro-2-(6-(4-(4-(oxetan-3-yl)piperazin-1-yl)phenylamino)-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-2-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)benzyl acetate 
• 1433824-29-3 4-fluoro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 
• 1433990-45-4 methyl 3-formyl-5,6,7,8-tetrahydroindolizine-2-carboxylate 
• 1433824-25-9 2-bromo-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]-indolizin-2(1H)-yl)benzyl acetate 
• 1433990-47-6 2-bromo-4-fluoro-6-(1-oxo-6,7,8,9-tetrahydropyridazino[4,5-b]indolizin-2(1H)-yl)benzaldehyde 
• 1346669-67-7 2-(2-(hydroxymethyl)-3-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl)phenyl)-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1(2H)-one 
• 1346672-98-7 2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)-6-(4-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 
• 1346672-97-6 2-bromo-6-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)benzyl acetate 
• 1346672-96-5 3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1(2H)-one 

Relevant academic research and scientific papers

A One-pot Three Carbon Decarboxylative Ring Expansion of Cyclic Secondary Amino Acids. X-Ray Crystal Structure of a Substituted 1-Azacyclo-octa-2,4-diene

Heating cyclic secondary α-amino acids with an excess of paraformaldehyde or formalin and methyl propiolate or dimethyl acetylenedicarboxylate leads to a decarboxylative ring expansion giving 8- and 9-membered cyclic aza-dienes via an azomethine ylide; the X-ray crystal structure of a substituted 1-azacyclo-octa-2,4-diene shows it to have an irregular tub conformation.

X=Y-ZH Systems as Potential 1,3-Dipoles. Part 42. Decarboxylative Three Carbon Ring Expansion of Cyclic Secondary α-Amino Acids via Azomethine Ylide Formation.

Cyclic 5- and 6-membered secondary α-amino acids react with formaldehyde and acetylenic dipolarophiles via azomethine ylide formation, cycloaddition and subsequent ring expansion to give 8- and 9-membered rings respectively.Ring expansion occurs by reaction of the bridgehead nitrogen of the initial bicyclic cycloadduct with a further molecule of dipolarophile to give a zwitterion which triggers the ring expansion.Dynamic p.m.r. studies show that ring inversion between pairs of mirror image conformations of the medium ring products are occuring with inversion barriers of 13-14.6 kcal/mol.