Benzomorphans: synthesis, stereochemistry reactions, and spectroscopic characterizations

Superelectrophiles in heterocyclic ring-forming reactions

“…55) and it involves the formation of a distonic superelectrophile (54, eq 17). 32 Protonation of the olefinic group and nitrogen atom gives the 1,4-dication 54, which cyclizes to form the desired heterocyclic ring system (55). There are two important aspects in the success of this chemistry.…”

Synthesis of 1‐(substituted phenylcarbonyl/sulfonylamino)‐1,2,3,6‐tetrahydropyridine‐5‐carboxylic acid diethylamides as potential anti‐inflammatory agents

“…Earlier work [12,13] by Knaus and co-workers indicated the synthesis of a series of N-(carbonylamino)-1,2,3,6-tetrahydropyridines (THPs) which showed anti-inflammatory, analgesic and hyperglycemic activities with no observed toxicities. Tetrahydropyridines are also important starting materials for the synthesis of benzomorphans, compounds with an analgesic activity similar to that of the morphinans [14,15]. It became evident that the pharmacological activities of the THP derivatives depended greatly on the position and nature of the substitutents on the THP ring structure [12,16,17].…”

“…The synthesis of the target compounds (7) is shown in Scheme 1 and the synthesis of the target compounds (15) is shown in Scheme 2. In Scheme 1, 1-chloro-2,4-dinitrobenzene (3) was reacted with N,N-diethyl nicotinamide (2) in acetone under reflux for 12 hours.…”

HPLC separation of pentazocine enantiomers in serum using an ovomucoid chiral stationary phase

“…Therefore the ( + ) cis or u enantiomer has the configuration 2s 6s 11s. The absolute configurations are shown in the figure (Palmer and Strauss, 1977). ( + ) Pentazocine is the more biologically active enantiomer and ( -) pentazocine is the less active enantiomer.…”