78266-67-8

Upstream product

• 201230-82-2 carbon monoxide 
• 579-71-5 2-nitrostyrene 
• 612-22-6 2-nitro(ethylbenzene) 
• 30096-07-2 methyl α-methyl-2-nitrobenzeneacetate 
• 64987-77-5 2-(2-nitrophenyl)propanol 

Downstream Products

• 83-34-1 3-Methylindole 
• 603-76-9 1-methylindole 
• 1296698-79-7 (S)-di-tert-butyl 1-(2-(2-nitrophenyl)-1-oxopropan-2-yl)hydrazine-1,2-dicarboxylate 

Relevant academic research and scientific papers

Asymmetric approach towards the total synthesis of (+)-actinopyllic acid

This paper describes our efforts towards the asymmetric total synthesis of (+)-actinophyllic acid. Starting from the chiral oxazolidinone 9, an azocino [4,3-b]indolyl intermediate (5) possessing the A/B/C ring system and the C16 quaternary stereogenic center of actinophyllic acid has been synthesized. Key steps include a LHMDS-promoted condensation to establish the critical C2–C16 bond and a successive four-step transformation to assemble the eight-membered C-ring of the target molecule.

(±)-cis-4a-alkyl-1,3,4,4a,9,9a-hexahydro-2H-carbazol-2-ones by domino nitro reduction-aza-Michael addition to enones

A domino nitro reduction-aza-Michael addition sequence has been investigated for α,β-unsaturated ketones and compared with the analogous reaction for conjugated esters. As expected, six-membered ring closures of ketones did not proceed as well as for esters (85%) due to the greater inherent reactivity of the ketones. This problem was minimized by performing the cyclization at lower temperature for a shorter time. The process has been extended to a synthesis of (±)-cis-4a-alkyl-1,3,4,4a,9,9a-hexahydro-2H-carbazol-2-ones with good yields (65%–86%). While the rigidity of the system and closure of the smaller five-membered ring created some strain in the products, yields were acceptable. The cis ring junction resulted from axial attack to give a more stable chair-like enol that tautomerized to the target heterocycle.

Catalytic Synthesis of 3-Substituted Indoles using CO as Building Block and Supported Rhodium as Catalyst

Under hydroformylation conditions, using supported rhodium as catalyst, 2-nitrostyrene is directly converted into skatole in ca. 70percent yield, by a reaction involving formation of 2-(o-nitrophenyl)propionaldehyde by homogeneous catalysis, reduction of the nitro-group by heterogeneous catalysis, then ring closure and thermal dehydration.