1616873-89-2

Upstream product

• 536-74-3 phenylacetylene 
• 89466-25-1 1-bromo-2-formylcyclopentene 
• 30928-55-3 2-(phenylethynyl)cyclopent-1-enecarbaldehyde 
• 106-47-8 4-chloro-aniline 
• 868-85-9 Dimethyl phosphite 

Downstream Products

• 1616874-31-7 dimethyl 3-benzyl-2-(4-chlorophenyl)-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-1-ylphosphonate 
• 1616874-63-5 dimethyl 3-benzoyl-2-(4-chlorophenyl)-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-1-ylphosphonate 

Relevant academic research and scientific papers

Formation of condensed 1 H-pyrrol-2-ylphosphonates and 1,2-dihydropyridin- 2-ylphosphonates via Kabachnik-fields reaction of acetylenic aldehydes and subsequent 5-exo-dig or 6-endo-dig cyclizations

Kabachnik-Fields reactions of various carbocyclic or heterocyclic acetylenic aldehydes together with subsequent Lewis acid catalyzed cyclizations have been studied. It was found that 5-exo-dig versus 6-endo-dig cyclization mode strongly depends on the structure of starting materials. Thus, nonaromatic acetylenic α-anilinomethylphosphonates underwent gold(III)-catalyzed or iodine-mediated 5-exo-dig cyclization to 1H-pyrrol-2-ylphosphonates. In contrast, electron-withdrawing heteroaromatic substrates formed 1,2-dihydropyridin-2-ylphosphonate ring containing materials via an exclusive 6-endo-dig ring-closure process. The dual mode of cyclization is possible only for α-amino (2-alkynylphenyl)methylphosphonates containing a benzene ring.