6515-01-1Relevant academic research and scientific papers
Selective synthesis of octahydroacridines and diannelated pyridines over zinc-containing mesoporous aluminosilicate molecular sieve catalysts
Selvaraj, Manickam,Assiri, Mohammed A.
, p. 12986 - 12995 (2019/09/06)
We demonstrate a very eco-friendly and single-step catalytic method for the highly selective synthesis of 1,2,3,4,5,6,7,8-octahydroacridine (OHA) by the vapour phase aminocyclization of cyclohexanone (CyO) with a mixture of formaldehyde (HCHO) and ammonia (NH3) over mesoporous bimetallic ZnAlMCM-41 (ZnAl-41) molecular sieves as efficient catalysts, which were synthesised by a simple basic hydrothermal method. To find optimum parameters for the synthesis of OHA, different reaction parameters, such as temperature, time on stream (TOS), weight hourly space velocity (WHSV), and feed molar ratios of CyO:HCHO:NH3, have been extensively studied. The used ZnAl-41 catalysts were treated by washing and calcination to recover the recyclable catalysts which were then reused in these reactions to study their catalytic abilities. To selectively synthesize a variety of pyridine compounds, the active mesoporous catalysts, namely, ZnAl-41(75) and recyclable ZnAl-41(75), with different reaction parameters, were extensively used in the vapour phase aminocyclization reaction with different aldehydes and cycloketones, and produced excellent product selectivities, e.g., 9-alkyl substituted octahydroacridines (9-ASOHAs) and diannelated pyridines (DAPs), with good ketone conversions. In this catalytic reaction, OHA, 9-ASOHAs and DAPs are the main products and are important as starting materials in the preparation of biologically active compounds, drugs, dyes and alkaloids. It is shown by our remarkable catalytic results that the ZnAl-41(75) catalyst, as an environmentally friendly heterogeneous catalyst, has outstanding catalytic activity in the production of OHA, 9-ASOHAs and DAPs by a single-step synthetic method.
Catalyzed hydrogenation of condensed three-ring arenes and their N-heteroaromatic analogues by a bis(dihydrogen) ruthenium complex
Borowski, Andrzej F.,Vendier, Laure,Sabo-Etienne, Sylviane,Rozycka-Sokolowska, Ewa,Gaudyn, Alicja V.
, p. 14117 - 14125 (2013/01/15)
A series of anthracene and acridine derivatives were hydrogenated under mild reaction conditions (80 °C, 3 bar of H2) using the bis(dihydrogen) complex [RuH2(η2-H2) 2{P(C6H11)3}2] (1) as a catalyst precursor. The influence of a methyl substituent on the substrate was studied. In all our systems, hydrogenation was only observed at the external rings leading to the corresponding 4H- or 8H-derivatives of anthracene and acridine. Three complexes resulting from the η4(C,C)-coordination of the substrate to the unsaturated fragment [RuH2{P(C 6H11)3}2] were characterized. In the case of 9-methyl acridine, the corresponding complex [RuH2(η 4-C14H11N){P(C6H11) 3}2] (4) turned out to be an active catalyst precursor leading to 1,2,3,4,5,6,7,8-octahydro-9-methylacridine as the sole product after 24 h. Regeneration of 1 from 4 supports the role of complex 4 in the catalytic cycle. Three hydrogenated products, 1,2,3,4-tetrahydroanthracene (4H-Anth), 1,2,3,4-tetrahydro-9-methylanthracene (4H-9-Me-Anth) and 1,2,3,4- tetrahydroacridine (4H-Acr), were characterized by X-ray diffraction. The Royal Society of Chemistry 2012.
SYNTHESIS OF HETEROCYCLES FROM 1,5-DIKETONES: 3.* ALICYCLIC 1,5-DIKETONES IN REACTION WITH PHENYLHYDRAZINE
Moskovkina, T. V.,Tilichenko, M. N.
, p. 38 - 44 (2007/10/02)
8-R-7aH-5,6,7,8,9,10,11,12-Octahydroindoloacridines, 1,2,3,4-tetrahydrocarbazole,9-R-sym-octahydroacridines, and 9-R,10-phenyl-sym-octahydroacridinium salts are formed by the action of phenyl-hydrazine on alkylidene-2,2'-dicyclohexanine or the corresponding 8-R-tricyclo(7.3.1.02,7)tridecan-2-ol-13-ones in an acid medium.Postulations were made for the paths of formation of these compounds. 2,2-Dimethyl-3-oxa-4a-(2',2'-dimethyltetrahydropyran-4'-on-5'yl-methyl)4aH-1,2,3,4-tetrahydrocarbazole, 3,3,14,14-tetramethyl-2-oxa-5a,10b-(methanoxyisobutane)-1,2,3,4,5a,10b,11,11a-octahydroquinindoline, 2,2-dimethyl-3-oxa-1,2,3,4-tetrahydrocarbazole and 3,3,6,6-tetramethyl-2,7-dioxa-sym-octahydroacridine were obtained by the reaction of methylene-3,3'-di(6,6-dimethyltetrahydropyran-4-one)with phenylhydrazine in acetic acid.The quinindoline structure was confirmed by the synthesis of this compound from 2,2-dimethyl-3-oxa-4a-(2',2'-dimethyltetrahydropyran-4'-on-5'-ylmethyl)-4aH-1,2,3,4-tetrahydrocarbazole by the action of ammonia.
