Hydroacridines: Part 30. ¹H and ¹³C NMR spectra of 9‐substituted 1,2,3,4,5,6,7,8‐octahydroacridines and of their N‐oxides

Abstract

The 1H and 13C NMR chemical shifts of 1,2,3,4,5,6,7,8-octahydroacridine, 12 of its 9-substituted derivatives, and of the corresponding N-oxides were determined, assigned, and discussed in terms of 9-substituent effects and effects of N-oxidation. A good linear correlation was found between the 13C chemical shifts of the aromatic carbons in octahydroacridines and those of respective carbons in the corresponding N-oxides.

Schiff bases containing a furoxan moiety as potential nitric oxide donors in plant tissues

“…Assigning the site of N -oxidation in various natural or biological active compounds is important both for structural and mechanistic purposes related to metabolisation of these compounds. We have also previously investigated the influence of N -oxidation on 15 N- and 13 C-NMR spectra for series of octahydroacridines [ 50 , 51 ]. The shifts induced by N -oxidation to C-alpha (C3 in furoxan derivatives) and C-beta (C4 in furoxan derivatives) is consistent with our previous studies [ 51 ], and with early data on simple furoxan derivatives [ 52 ].…”

“…We have also previously investigated the influence of N -oxidation on 15 N- and 13 C-NMR spectra for series of octahydroacridines [ 50 , 51 ]. The shifts induced by N -oxidation to C-alpha (C3 in furoxan derivatives) and C-beta (C4 in furoxan derivatives) is consistent with our previous studies [ 51 ], and with early data on simple furoxan derivatives [ 52 ]. The N -oxidation induces a significant shielding of the C-alpha and a slight deshielding of the C-beta in the 13 C-NMR spectra.…”

Pyridine Compounds with Antimicrobial and Antiviral Activities

“…Marinescu et al [ 23 , 24 , 25 , 26 , 27 , 28 ] synthesized a series of tetrasubstituted pyridine-N-oxides (octahydroacridines) 38–41 , starting from the reaction of 2,2′-methylenedicyclohexanone with formamide at 167–170 °C and the separation of 1,2,3,4,5,6,7,8-octahydroacridine 36 from the reaction mixture ( Scheme 7 ). Oxidation of compound 36 with hydrogen peroxide and acetic acid gave the key intermediate 37 , sym -octahydroacridine-10-oxide, which, through reactions of nitration, reduction, alkylation, and hydrolysis, gave the compounds 38 , 39 , 40, and 41 .…”

Octahydroacridine thin films grown by matrix-assisted pulsed laser evaporation for non linear optical applications

“…One such compound is 1,2,3,4,5,6,7,8-octahydroacridine (C 13 H 17 N) or OHA, a white crystalline solid that is less toxic compared to acridine [11,12]. OHA and its derivatives are of great interest as they play an important role in the preparation of agrichemicals, alkaloids, dyes, medicines, drugs and other biologically active compounds with intriguing pharmacological and therapeutic properties in cancer and Alzheimer's disease treatments, and advanced functional materials precursors [1,2,13,14].T o d a y , OHA can be easily synthesized by different routes [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30], making it an economically attractive candidate for various applications due to its excellent price/quality ratio. Among these applications, non-linear optical (NLO) properties that may arise from particularities of the OHA molecule (i.e.…”