95683-74-2

Upstream product

• 113789-90-5 ethyl 2-(3'-azidopropyl)pent-4-enoate 
• 178172-33-3 tert-butyl 3-allyl-2-oxopiperidine-1-carboxylate 
• 675-20-7 piperidin-2-one 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 5693-62-9 2,3,4,5-tetrahydro-6-methoxypyridine 
• 907561-25-5 5-allyl-6-methoxy-2,3,4,5-tetrahydro-pyridine 
• 14660-52-7 ethyl 5-bromovalerate 
• 89896-39-9 ethyl 5-azidovalerate 
• 67-56-1 methanol 
• 1215765-30-2 3-allyl-1-chloropiperidin-2-one 
• 2622-05-1 allylmagnesium bromide 
• 106-95-6 allyl bromide 

Downstream Products

• 942413-09-4 C₁₇H₁₇F₆NO 
• 89656-44-0 2‐allylpiperidine 

Relevant academic research and scientific papers

COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF

Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

Photochemical rearrangement of N -chlorolactams: A route to N -heterocycles through concerted ring contraction

We report a novel ring contraction allowing the direct conversion of N-chlorolactams to their corresponding ring-contraction N-heterocycles upon photolysis. Results show that the rearrangement occurs with a variety of N-chlorolactams and that the greater the substitution at the migrating carbon, the greater the yield of product. Importantly, stereochemistry at the migrating carbon is conserved in the product. Rearranged products were isolated as their methyl carbamates in yields varying from 17% to 58%, with the major side product being the recyclable parent lactam.

SUBSTITUTED OXAZOLIDINONES AND THEIR USE

The invention relates to novel substituted oxazolidinones, to processes for preparation thereof, to the use thereof for treatment and/or prophylaxis of diseases, and to the use thereof for producing medicaments for treatment and/or prophylaxis of diseases

Radical allylations by reaction of azides with allylindium dichloride

Allylindium dichloride is an effective reagent for carrying out photolytically initiated radical allylation reactions, as also proved by EPR experiments. In the presence of suitable azides that can give rise to electrophilic radicals, a homolytic chain reaction occurs with formation of allylated compounds. With δ-azido esters and chlorides generation of primary indiumaminyl radicals is followed by a very efficient 1,5-H shift process that gives rise to electrophilic carbon-centred radicals, whose subsequent allylation by the starting indium reagent, followed by aqueous workup, eventually affords allylated nitrogen heterocycles in good yields. Some comparative theoretical calculations accounted for the observation that analogous reactions with an organoallyltin reagent did not work at all. The results show that the reaction with allylindium dichloride seems strongly favoured by both a lower BDE of the allyl-metal bond and a considerably faster, exothermic 1,5-H migration step. The Royal Society of Chemistry 2010.

Discovery of 3-piperidinyl-1-cyclopentanecarboxamide as a novel scaffold for highly potent CC chemokine receptor 2 antagonists

Introduction of ring restrictions to a linear aminobutyramide CC chemokine receptor 2 (CCR2) antagonist lead (2) led to the discovery of a 1,3-disubstituted cyclopentane scaffold with enhanced hCCR2 receptor binding and antagonist activity. (1S,3R)-N-[3,5

An aza-enolate alkylation strategy for the synthesis of α-alkyl-δ-amino esters and α-alkyl valerolactams

Alkylation of the aza-enolate of valerolactim methyl ether with electrophiles affords α-alkyl lactims that may be hydrolysed under mild acidic conditions to afford their corresponding α-alkyl-δ-amino esters as their hydrochloride salts. Neutralisation of these salts with base results in smooth intramolecular cyclisation to afford their corresponding α-alkyl lactams in excellent yield. Georg Thieme Verlag Stuttgart.

SYNTHESIS AND REACTIVITY OF METHYL γ-AZIDO BUTYRATES AND ETHYL δ-AZIDO VALERATES AND OF THE CORRESPONDING ACID CHLORIDES AS USEFUL REAGENTS FOR THE AMINOALKYLATION

The azidoesters 13 and 14 and the corresponding acid chlorides 22 and 23 are shown to be interesting reagents for the nucleophilic and electrophilic aminoalkylation. α-substituted methyl γ-azidobutyrates 13 and ethyl δ-azido valerates 14 are easily accessible by alkylation of the lithium enolates of the parent compounds 13a and 14a respectively.Their chemoselective reduction leads to 3-substituted lactams 18 and 19.The acid chlorides 22 and 23 issued from 13 and 14 react with nucleophilic reagents, i.e. the carbanion of Meldrum acid, trimethylphosphite and n-butylmanganous iodide giving the the ω-azido,β-ketoesters 25 and 26, the ω-azido,α-acylphosphonates 29 and 30 and the ω-azido ketones 38 and 39 respectively in good yields.The treatment of 25 and 26 by Ph3P in anhydrous ether leads to the cyclic β-enaminoesters 27 and 28 whereas the α-acylphosphonates give the cyclic iminophosphonates 33 and 34a in good yields.These cyclizations occur via an intramolecular aza-Wittig reaction.