14465-61-3

Usage

Synthesis Reference(s)

Tetrahedron, 61, p. 155, 2005 DOI: 10.1016/j.tet.2004.10.035

InChI:InChI=1/C11H13N/c1-11(2)8-7-9-5-3-4-6-10(9)12-11/h3-8,12H,1-2H3

Upstream product

• 7471-09-2 3-methyl-3-phenylamino-1-butyne 
• 1002109-61-6 (E)-4-(2-aminophenyl)-2-methylbut-3-en-2-ol 
• 62-53-3 aniline 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 615-36-1 2-bromoaniline 
• 615-43-0 2-iodophenylamine 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 20364-30-1 2,2-dimethyl-1,2,3,4-tetrahydroquinoline 
• 88774-00-9 N-(2-trifluoromethylbenzoyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline 
• 179898-87-4 1-tert-butoxycarbonyl-1,2,3,4-tetrahydro-2,2-dimethyl-4-quinolinone 
• 201541-36-8 1,2,3,4-tetrahydro-2,2-dimethyl-7-nitroquinoline 
• 179899-22-0 7-amino-1,2,3,4-tetrahydro-2,2-dimethylquinoline 
• 179899-03-7 (R/S)-3-ethyl-1,2,3,4-tetrahydro-2,2-dimethylquinoline 
• 179898-88-5 1,2,3,4-tetrahydro-2,2,3-trimethylquinoline 
• 179898-89-6 1-tert-butoxycarbonyl-1,2-dihydro-2,2-dimethylquinoline 

Relevant academic research and scientific papers

SUBSTITUTED, SATURATED AND UNSATURATED N-HETEROCYCLIC CARBOXAMIDES AND RELATED COMPOUNDS FOR THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS

The invention provides substituted, saturated and unsaturated N-heterocyclic carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.

Enantioselective Synthesis of 4-Cyanotetrahydroquinolines via Ni-Catalyzed Hydrocyanation of 1,2-Dihydroquinolines

A Ni-catalyzed asymmetric hydrocyanation that enables the formation of 4-cyanotetrahydroquinolines in good yields with excellent enantioselectivities is presented herein. A variety of functional groups are well-tolerated, and a gram-scale reaction supports the synthetic potential of the transformation. Additionally, several crucial intermediates for pharmaceutically active agents, including a PGD2 receptor antagonist, are now accessible through asymmetric synthesis using this new protocol.

Enantioselective epoxidation of dihydroquinolines by using iminium salt organocatalysts

The first examples of asymmetric epoxidation of dihydroquinoline substrates using iminium salt organocatalysts are reported. The 3,4-epoxytetrahydroquinoline products are obtained in good yields and with moderate to good enantioselectivities.

Chemoselective palladium-catalyzed reaction in aqueous media: Selectivity in the reaction of haloanilines with 1,1-dimethylallyl alcohol

Palladium-catalyzed reactions of various haloanilines with 1,1-dimethylallyl alcohol were carried out in the presence of a hydrophilic ligand, 3,3′,3″-phosphinidyne tris(benzenesulfonic acid) trisodium salt (TPPTS), or a lipophilic phosphine ligand, 1,1′- bis(diphenylphosphino)ferrocene (DPPF). The reactions proceeded chemoselectively in aqueous solvent to give C-vinylated products under basic conditions or N-allylated products under neutral conditions in practical yields (up to 79%). The use of an aqueous solvent played an important role in this chemoselectivity and allowed the development of a one-pot synthesis of 3-methylindole. This chemoselectivity is synthetically useful because the reactive position of haloanilines can be controlled simply by changing the basicity of the reaction medium, which eliminates the need to protect the amino group during the reaction.

ALKOXYPHENYLPROPANOIC ACID DERIVATIVES

The present invention aims at provision of a novel compound having a GPR40 receptor function modulating action, which is useful as an insulin secretagogue, an agent for the prophylaxis or treatment of diabetes and the like. The compound represented by the formula: wherein each symbol is as defined in the description, a salt thereof, and a prodrug thereof of the present invention unexpectedly have a superior GPR40 receptor agonistic activity and superior properties as pharmaceutical products such as stability and the like, and can be safe and useful pharmaceutical agents as agents for the prophylaxis or treatment of GPR40 receptor-related pathology or diseases in mammals.

The preparation and some chemistry of 2,2-dimethyl-1,2-dihydroquinolines

The cyclisation of N-(1,1-dimethylpropargyl) anilines, using cuprous chloride in refluxing toluene, yields 6-substituted-2,2-dimethyl-1,2- dihydroquinolines. The reactivity of the double bond in the heterocyclic ring of these products is exemplified by chlorination, to yield 6-substituted-3,4-cis- dichloro-2,2-dimethyl-1,2,3,4-tetrahydroquinolines which can be selectively dechlorinated to provide 6-substituted-3-chloro-2,2-dimethyl-1,2,3,4- tetrahydroquinolines; epoxidation to yield an epoxide, which can be hydrogenolysed to the corresponding 3-hydroxy product and in turn oxidised to the 3-keto derivative; and oxymercuration to provide a 4-hydroxy product and hence a 4-keto derivative. Dehydrochlorination of a 3,4-dichloro product provides a 3-chloro-1,2-dihydroquinoline which can be hydrolysed to a 3-keto system. The formation of cis 3,4-dichloro products from the chlorination, as well as the formation of a cis chlorohydrin from the chlorination of N-acetyl-2,2,6-trimethyl-1,2-dihydroquinoline in partially aqueous solution, suggests that N-acetyl, or N-trifluoroacetyl groups, participate in the addition process. Graphical Abstract.

Androgen receptor modulator compounds and methods

Non-steroidal compounds that are high affinity, high selectivity modulators for androgen receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring androgen receptor agonist, partial agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the androgen receptor modulator compounds.

Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2- dihydropyridono[5,6-g]quinolines

A new nonsteroidal antiandrogenic pharmacophore has been discovered using cell-based cotransfection assays with human androgen receptor (hAR). This series of AR antagonists is structurally characterized by a linear tricyclic 1,2-dihydropyridono[5,6-g]quinoline core. Analogues inhibit AR- mediated reporter gene expression and bind to AR as potently as or better than any known AR antagonists. Several analogues also showed excellent in vivo activity in classic rodent models of AR antagonism, inhibiting growth of rat ventral prostate and seminal vesicles, without accompanying increases in serum gonadotropin and testosterone levels, as is seen with other AR antagonists. Investigations of structure - activity relationships surrounding this pharmacophore resulted in molecules with complete specificity for AR, antagonist activity on an AR mutant commonly observed in prostate cancer patients, and improved in vivo efficacy. Molecules based on this series of compounds have the potential to provide unique and effective clinical opportunities for treatment of prostate cancer and other androgen-dependent diseases.

STEROID RECEPTOR MODULATOR COMPOUNDS AND METHODS

Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.