An imino-Diels–Alder route to meso-2,6-disubstituted-4-piperidones

Synthesis, Spectral and Computational Studies of some 2-(2-(3-Methyl-2,4-Diphenyl-3-Azabicyclo[3.3.1]Nonan-9-Ylidene)Hydrazinyl)Benzo[d]Thiazole Derivatives

“…Thiazoles are the important group of heterocyclic compounds due to their drug utility [13]. In continuation of our earlier work some 2-(2-(3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazinyl)benzo [d]thiazoles (11)(12)(13)(14) were synthesized in the present study and their conformational behaviour was analyzed using 1 H and 13 C NMR spectroscopy. The preferred conformations were further confirmed by means of conformational analysis performed by DFT calculations.…”

“…After cooling, the product was filtered and then washed with water. The products (11)(12)(13)(14) were purified by column chromatography. All the synthesized compounds were obtained in good yield and their analytical data are given in Table 1 and their synthetic methodology is given in Scheme 1 ( …”

“…Recently attention has been focused on the application of the piperidone derivatives as prospective biophotonic materials [9,10]. Since the pharmacological properties and the reactivity depend on their stereochemistry, efforts were made for the development of new synthetic techniques leading to stereoselective piperidines and their characterization [11,12]. Thiazoles are the important group of heterocyclic compounds due to their drug utility [13].…”

Proline‐Catalyzed Imino‐Diels–Alder Reactions: Synthesis of meso‐2,6‐Diaryl‐4‐piperidones

“…[5] Recently, we described an efficient method for the stereoselective synthesis of meso-2,6-disubstituted-4-piperidones by the imino-Diels-Alder reaction of 3-unsubstituted-2-aminodienes using CuA C H T U N G T R E N N U N G (OTf) 2 as a Lewis acid catalyst ( Figure 1). [6] In this case, it was necessary to prepare and isolate the 2-amino-1,3-diene reactant in advance in order for this reaction to be successful.…”

Regio- and Chemoselective Unprecedented Imino-Diels-Alder Reactions of 1-Substituted Unactivated Dienes with N-Aryl Imines - Part II

“…3,4 In contrast such reactions involving the use of unactivated dienes are scarcely accessible in literature. 5 Also, the catalysed methodology has not been effectively explored for the participation of N-aryl imines as 4p components in imino-Diels-Alder reactions with unactivated dienes. 6 Kobayashi et al reported the use of transitionmetal salts as catalysts in aza-Diels-Alder reactions of Naryl imines with unhindered activated alkenes, furan, cyclopentadiene, and symmetrical activated butadienes leading to the synthesis of tetrahydro-and dihydroquinoline, tricyclic di-and tetrahydrofuranoquinoline, and diand tetrahydropyridine derivatives, respectively.…”