17336-90-2

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 2242, 1956 DOI: 10.1021/ja01591a059

InChI:InChI=1/C11H11NO/c1-7-8(2)11(13)12-10-6-4-3-5-9(7)10/h3-6H,1-2H3,(H,12,13)

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 88426-94-2 3-methyl-2-hydroxytryptophol 
• 941706-81-6 1-(2-aminophenyl)ethanol 
• 88426-92-0 α-(o-nitrophenyl)-α-methyl-γ-butyrolactone 
• 1823-91-2 1-phenylethyl cyanide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 133901-59-4 2-(2-aminophenyl)but-2-ene 
• 124-38-9 carbon dioxide 
• 62-53-3 aniline 
• 60751-77-1 propionic acid-(2-acetyl-anilide) 
• 20717-39-9 2-methyl-3-oxo-N-phenylbutanamide 
• 30931-93-2 α-methyl-α-phenyl-γ-butyrolactone 

Relevant academic research and scientific papers

Lactamization of alkenyl C-H bonds to generate 2-quinolinones with triphosgene

A simple and easy-going method is developed to synthesize the analogues of 2-quinolinones by using triphosgene (BTC) as the carbonyl source. In these reactions, both the toxic carbon monoxide (CO) and phosgene are avoided and the 2-quinolinones are obtained in moderate to good yields under mild conditions, all of which are anticipated to be meaningful in both industry and laboratory.

Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral

The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.

The formation of quinolin-2(1H)-ones via electrocyclic reaction of o-isocyanatostyrenes generated in situ from o-isocyanostyrenes

A convenient one-pot preparation of 4-substituted or 3,4-disubstituted quinolin-2(1H)-ones from 2-isocyanostyrene derivatives, which involves mCPBA oxidation to the corresponding isocyanate intermediates followed by electrocyclization, is described.

Synthesis of 5,8-Dimethoxy-2(1H)-quinolinones by Intramolecular Wittig Reaction

The title compounds 12, which are key intermediates for antitumoral diazaquinomycin A analogues, are obtained by intramolecular Wittig reaction of 1-alkyltriphenylphosphonium salts 11, which are prepared via lithiation of 2',5'-dimethoxy-N-pivaloylaniline 6.The applicability of this route to polysubstituted 2(1H)-quinolinones 12 and 17 is examined. - Keywords: Wittig reaction / 2(1H)-Quinolinones / ortho-Directed metalation of anilides

Reactions of 2-Hydroxytryptophol: Results of Strong Acid and Alkaline Treatments of 2-Hydroxytryptophol

Upon being warmed at 90 deg C in trifluoromethanesulfonic acid for 42-78 h, 2-hydroxytriptophol (4a) gave 3-ethylideneoxidoles (E- and Z-form) (5a), while 3-methyl- (4b) or 3-ethyl-2-hydroxytryptophol (4c) gave the corresponding 3-alkylideneoxindoles (5b,