194979-77-6

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-3,4-Dihydro-2(1H)-quinolinone is used as a synthetic intermediate for the preparation of benzo[c]quinolizin-3-ones. These compounds are potent and selective nonsteroidal inhibitors of human steroid 5α-reductase 1, an enzyme involved in the conversion of testosterone to dihydrotestosterone (DHT). Inhibiting this enzyme can be beneficial in treating conditions such as benign prostatic hyperplasia (BPH) and androgenetic alopecia (male pattern baldness).

Upstream product

• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 501-52-0 3-Phenylpropionic acid 
• 645-45-4 hydrocinnamic acid chloride 

Downstream Products

• 1070955-54-2 C₁₄H₁₉NO₄ 
• 518285-15-9 1-tert-butoxycarbonylamino-2-(3-hydroxypropyl)benzene 
• 1394031-54-9 tert-butyl 2-(1-phenyl-1H-imidazole-2-carbonyl)indoline-1-carboxylate 
• 1394031-49-2 tert-butyl 2-benzoylindoline-1-carboxylate 
• 1394031-38-9 tert-butyl 2-(3-oxo-3-(1-phenyl-1H-imidazol-2-yl)propyl)phenylcarbamate 
• 1394031-32-3 tert-butyl (2-(3-oxo-3-phenylpropyl)phenyl)carbamate 
• 944467-32-7 tert-butyl 2-hydroxy-3,4-dihydroxy-3,4-dihydroquinone-1(2H)-carboxylate 

Relevant academic research and scientific papers

Synthesis of benzo[c]quinolizin-3-ones: Selective non-steroidal inhibitors of steroid 5α-reductase 1

A short and efficient synthesis of novel benzo[c]quinolizin-3-one derivatives is described. The synthesis is based on the tandem Mannich- Michael cyclization between 2-silyloxy-1,3-butadienes and a N-t-Boc iminium ion. The prepared derivatives are selective inhibitors of human steroid 5α- reductase isoenzyme 1, thus having potential application as drugs for treatment of male pattern baldness and other DHT-dependent skin disorders.

TMSOTf-mediated approach to 1,3-oxazin-2-one skeleton through one-pot successive reduction-[4 + 2] cyclization process of imides with ynamides

A one-pot approach to access functionalized 1,3-oxazin-2-one skeleton has been developed through successive reduction and subsequent [4 + 2] cyclization process of N-Boc lactams with ynamides by TMSOTf. As a result, a number of five to seven membered ring fused bicyclic [1,2-c][1,3]oxazin-1-ones 12a-m and tricyclic derivatives 13a-f were obtained in moderate to excellent yields with excellent regioselectivities. Moreover, linear N-Boc amides 9a-e were also amenable to this transformation, and the desired 3,4-dihydro-1,3-oxazin-2-ones 14a-m were readily achieved in moderate yields with excellent regioselectivities.

Visible-Light Induced C(sp2)?H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover

We report an approach for the intramolecular C(sp2)?H amidation of N-acyloxyamides under photoredox conditions to produce δ-benzolactams with an aryl-alkyl σ-bond relocation. Computational studies on the designed reductive single electron transfer strategy led us to identify N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor. Upon the formation of an azaspirocyclic radical intermediate by the selective ipso-addition with outcompeting an ortho-attack, radical–polar crossover was then rationalized to lead to the rearomative ring-expansion with preferential C?C bond migration.

KRAS G12C INHIBITORS AND USES THEREOF

The invention relates to compounds of Formula I, and pharmaceutically acceptable salts thereof, and methods of making and using the same. The compounds of the invention are effective in inhibiting KRAS protein with a G12C mutation and are suitable for use in methods of treating cancers mediated, in whole or in part, by KRAS G12C mutation.

Palladium-Catalyzed Asymmetric Heck-Matsuda Reaction of 1,4-Dihydroquinolines with Aryl Diazonium Salts

A palladium-catalyzed asymmetric Heck-Matsuda reaction of N -Boc-1,4-dihydroquinolines and aryl diazonium tetrafluoroborates is realized in moderate to high yields and with high enantioselectivities. The method provides an efficient route to access optically active 2-arylhydroquinolines.

A one-pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines: Via asymmetric reductive amination (ARA)

Asymmetric reductive amination for the synthesis of both chiral tetrahydroquinolines (THQs) and tetrahydroisoquinolines (THIQs) has been realized with an Ir/ZhaoPhos catalytic system via a one-pot N-Boc deprotection/intramolecular asymmetric reductive amination (ARA) sequence. Control experiments reveal that HCl plays a vital role to the success of this transformation. The HCl acid assists the removal of the N-Boc protecting group and also provides chloride ions to interact with the thiourea moiety in ZhaoPhos, thus leading to excellent reaction enantiocontrol.

RORγ MODULATORS

Described are RORγ modulators of the formula (I), or pharmaceutically acceptable salts thereof, wherein all substituents are defined herein. The invention includes stereoisomeric forms of the compounds of formula I, including stereoisomerically-pure, scalemic and racemic form, as well as tautomers thereof. Also provided are pharmaceutical compositions comprising the same. Such compounds and compositions are useful in methods for modulating RORγ activity in a cell and methods for treating a subject suffering from a disease or disorder in which the subject would therapeutically benefit from modulation of RORγ activity, for example, autoimmune and/or inflammatory disorders.

RORγ MODULATORS

Described are RORγ modulators of the formula (I), or pharmaceutically acceptable salts thereof, wherein all substituents are defined herein. The invention includes stereoisomeric forms of the compounds of formula I, including stereoisomerically-pure, scalemic and racemic form, as well as tautomers thereof. Also provided are pharmaceutical compositions comprising the same. Such compounds and compositions are useful in methods for modulating RORγ activity in a cell and methods for treating a subject suffering from a disease or disorder in which the subject would therapeutically benefit from modulation of RORγ activity, for example, autoimmune and/or inflammatory disorders.

METHOD FOR PRODUCING AROMATIC COMPOUND HAVING RING STRUCTURE THAT INCLUDES NITROGEN ATOM OR OXYGEN ATOM

The invention is a method for efficiently producing an aromatic compound by an intramolecular cyclization reaction, the aromatic compound having a ring structure that includes a nitrogen atom or oxygen atom. An aromatic compound composed of tert-butyl-2-(

Tetrahydroquinoline sulfonamides as vasopressin 1b receptor anatgonists

Vasopressin 1b (V1b) antagonists have been postulated as possible treatments for depression and anxiety. A novel series of potent and selective V1b antagonists has been identified starting from an in-house screen hit. The incorporation of a sulfonamide li