34421-99-3

Usage

Synthesis Reference(s)

Synthetic Communications, 18, p. 1475, 1988 DOI: 10.1080/00397918808081303

InChI:InChI=1/C11H13N/c1-3-8-7-9-4-2-6-11(9)12-10(8)5-1/h7H,1-6H2

Upstream product

• 55100-61-3 2,2'-methylenedicyclopentanone 
• 30469-91-1 threo-2,2'-methylenedicyclopentanone 
• 28051-68-5 methacrolein oxime 
• 120-92-3 cyclopentanone 
• 2611-03-2 2-chlorocyclopent-1-ene-1-carbaldehyde 
• 50-00-0 formaldehyd 
• 119476-42-5 2-Azido-1-cyclopentene-1-carboxaldehyde 
• 119476-44-7 2-(triphenylphosphoranylidene)amino 1-cyclopentene 1-carboxaldehyde 

Downstream Products

• 96413-25-1 α,α'-dibenzylidene-2,3:5,6-bis(trimethylene)pyridine 

Relevant academic research and scientific papers

Selective synthesis of octahydroacridines and diannelated pyridines over zinc-containing mesoporous aluminosilicate molecular sieve catalysts

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.

Vapor phase synthesis of annelated pyridines over metal modified zeolite beta

Vapor phase synthesis of annelated pyridines from cyclic ketones, aldehydes and ammonia was carried out over various zeolite molecular sieves like Hβ, HZSM-5 (240), HZSM-5 (40), HY, HX, HMCM-41 and Mordenite. The preliminary screening of catalyst clearly shows that Hβ catalyst was found to be more active for the vapor phase synthesis of annelated pyridines. Hβ was further modified with transition metals like Fe, Cu, Pb, Mo, Zn, Ni, Co, Ce, W and Sn to get higher yields.

Synthesis of alkyl- and aryl-substituted pyridines from (α,β-unsaturated) imines or oximes and carbonyl compounds

Reaction of a variety of (α,β-unsaturated) imines or oximes with aliphatic aldehydes or cyclic ketones in the presence of a secondary amine afforded alkyl-, and/or aryl-, and/or cycloalkyl-substituted pyridines. To explain their formation, a hetero Diels-Alder reaction has been postulated, in which an 1-aza-1,3-butadiene reacts with an in situ generated enamine.

SATURATED NITROGEN-CONTAINING HETEROCYCLES. 14. SYNTHESIS AND THREE-DIMENSIONAL STRUCTURES OF N-R-DICYCLOPENTAPIPERIDINES

The catalytic hydroamination of threo-methylenedicyclopentanone using ammonia, methylamine, and monoethanolamine as the aminating agents proceeds stereospecifically with the formation of N-R-cis-syn-cis-dicyclopentapiperidines (R=H, CH3, CH2CH2OH).The structures of the latter were proved by 13C NMR spectroscopy.The molecular structure of N-(β-hydroxyethyl)cis-syn-cis-dicyclopentapiperidinium acid tartrate was investigated by x-ray diffraction analysis, and the absolute configuration of its chiral centers was determined.

Certain 5,6,7,8-tetrahydroquinoline-8-thiocarboxamides

The invention relates to novel pyridine derivatives which have a fused 5,6, or 7-membered saturated hydrocarbon ring adjacent to the nitrogen of the pyridine ring, and a group X situated on said hydrocarbon ring and separated by one carbon atom from the pyridine nitrogen atom, said group X is cyano, CONHR3, CSNHR3 or CO2 R5 wherein R3 is selected from hydrogen, lower alkyl and lower aralkyl radicals and R5 is selected from hydrogen, lower alkyl and lower aralkyl radicals which may be substituted by alkyl, alkoxy, halogen, nitro or trifluoromethyl; other substituents may be present. Compounds wherein X is CSNHR3 are anti-ulcer agents and the other compounds are intermediates therefor.

Cyclopenteno[b]pyridine derivatives

The invention relates to novel cyclopenteno[b]pyridine derivatives which have a thioamide group in the 7-position and related tricyclic compounds. The compounds are anti-ulcer agents.

Cyclopenteno[b]pyridine derivatives

The invention relates to novel cyclopenteno[b]pyridine derivatives which have a group X on the 7-position and related tricyclic compounds. X is CONHR3, or CO2 R5 wherein R3 is hydrogen or lower alkyl and R5 is hydrogen or a lower alkyl or lower aralkyl group which may be substituted by alkyl, alkoxy, halogen, nitro or trifluoromethyl; other substituents may be present. The compounds are intermediates for compounds wherein X is CSNHR3 which are anti-ulcer agents.

Pharmaceutical compositions containing 5,6,7,8-tetrahydroquinoline derivatives and related compounds

The invention relates to pharmaceutical compositions containing 5,6,7,8-tetrahydroquinoline-8-thioamides and nitriles and related tricyclic compounds and methods of treating ulcers using said compounds.

Magnesium halide derivatives of tetrahydroquinolines

The invention relates to magnesium halide derivatives of tetrahydroquinolines and related compounds. These are intermediates useful in the preparation of anti-ulcer agents.