18159-32-5

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 35, p. 651, 1957 DOI: 10.1139/v57-094Tetrahedron, 52, p. 3705, 1996 DOI: 10.1016/0040-4020(96)00046-4

Upstream product

• 13652-31-8 N-(cyclohexylidene)isopropylamine 
• 7647-01-0 hydrogenchloride 
• 99176-23-5 2-(1,4-dioxaspiro[4.5]dec-6-yl)ethylamine 
• 109-99-9 tetrahydrofuran 
• 95192-95-3 (1,4-dioxaspiro[4.5]dec-6-yl)acetonitrile 
• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 1193-68-6 cis-octahydroindole 
• 2402-57-5 2-(2-chloroethyl)cyclohexanone 
• 87266-80-6 N-oxido-Δ¹⁽⁸⁾-hexahydroindole 

Downstream Products

• 101864-54-4 1-(3,4-dimethoxy-phenethyl)-2,3,4,5,6,7-hexahydro-indole 
• 101288-56-6 1-benzoyl-octahydro-indole-7a-carbonitrile 
• 13618-91-2 4,5,6,7-tetrahydroindole 
• 53924-05-3 7-chloro-1H-indole 
• 23456-78-2 1,4,5,6-tetrahydro-7H-indol-7-one 
• 114144-22-8 2,3-dihydro-7-chloro-1H-indole 

Relevant academic research and scientific papers

Photochemical rearrangement of oxaziridines and nitrones in the hexahydroindole series: A convenient synthetic route to 1-azabicyclo[5.2.0]nonan-2-ones as novel rgd mimetics

(equation presented) Photolysis of oxaziridines a or nitrones b provides a convenient synthetic route to fused bicyclic lactams c adequately substituted on both cycles A and B as scaffolds for mimicking conformationally constrained β-turn peptides as in the tripeptide RGD signaling motif of fibronectin.

Novel routes to indoles, indolines, quinolines and tetrahydroquinolines from N-(cyclohexylidene)amines

Cyclohexanones have been converted into a variety of bicyclic azaheterocycles of different oxidation level via a sequence of reactions involving (a) imination, (b) α-alkylation with N,N-disilyl-protected ω-bromoamines, (c) transimination, (d) α-chlorination of the resulting bicyclic imines and (e) dehydrochlorination and/or dehydrogenation. Appropriate choice of the reaction conditions selectively led to reactions to indoles, 7-chloroindoles, 7-chloroindolines, 4,5,6,7-tetrahydroindoles, 8-chloro-1,2,3,4-tetrahydroquinolines, 8-chloroquinolines or quinolines.

STEREOSELECTIVE SYNTHESIS OF THE TRICYCLIC CONDENSED DERIVATIVES OF THIAZOLIDINE

The perhydro derivatives of thiazoloquinoline, thiazolocyclopentapyridine, thiazoloindole, and cyclopentapyrrolothiazole and also their 2-methyl derivatives were synthesized by the addition of thiirane and methylthiirane at the C=N bond in bicyclic imines of the 2,3,4,4a,5,6,7,8-octahydroquinoline type.An alternative method involves reaction of the thiiranes with amino ketones of the 2,2-ethylenedioxycyclohexylpropylamine type, protected at the carbomyl group, followed by acid deblocking and cyclization by treatment with alkali.The last method is the only method for the production of perhydrocyclopentapyrrolothiazoles, since 2,3,3a,4,5,6-hexahydrocyclopentapyrrole is not a stable imine.Some of the compounds were obtained in the form of single diastereomers, the configurations of which for the two subjects were determined by NMR.In other cases mixtures of the stereoisomers are formed with a srtong preponderance of one of them; arguments concerning their configurations are presented.It is shown that both methods of synthesis lead to an identical stereochemical result.

Synthesis and Thermolysis of O-Alkyl-N-vinylhydroxylamine Derivatives

Oxoiminium salts 11 a-e and 13 a-e have been prepared from the ο-chloroketones 9 a-e by oximation via the cyclic oxime ethers 10 a-e and the cyclic imine oxides 12 a-e, followed by alkylation with "Meerwein salt".The deprotonation reaction of 11 a-e and 13 a-e yields, via the regioselectively prepared intermediates 14 a-e and 17 a-e, the α, β-unsaturated imines 15 a-e and the cyclic imines 18 a-e, respectively.