83463-88-1Relevant academic research and scientific papers
Synthesis of quinolines: Via sequential addition and I2-mediated desulfurative cyclization
Gao, Ziwei,Jian, Yajun,Sun, Huaming,Wang, Yanyan,Yang, Mingming,Zhang, Guofang,Zhang, Weiqiang
supporting information, p. 38889 - 38893 (2021/12/20)
An efficient one-pot approach for the synthesis of quinolines from o-aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed - a two-step Michael additi
Synthesis of substituted coumarins and 2-quinolinones by cycloisomerisation of (hydroxy/aminophenyl)propargyl alcohols
Sridhar Reddy, Maddi,Thirupathi, Nuligonda,Babu, Madala Hari
, p. 5803 - 5809 (2012/11/07)
A new cycloisomerization strategy for the synthesis of coumarins and quinolinones is described. The addition of ethoxyacetylide to 2-hydroxyacetophenones directly resulted in 4-substituted coumarins by 6-endo-dig cycloisomerisation of the intermediate 3-ethoxy-1-(2-hydroxyphenyl)- 2-propyn-1-ols. Under similar conditions, 2-aminoacetophenone produced 2-ethoxyquinoline, a masked quinolinone, which was converted into the quinolinone by acid treatment. N-Protected intermediate 8 was isolated and converted into the quinolinone [with In(OTf)3 or H2SO 4] or the 3-iodo-2-quinolinone (with I2 and H +).
Facile synthesis of 4-phenylquinolin-2(1H)-one derivatives from N-acyl-o-aminobenzophenones
Park, Kwanghee Koh,Lee, Jin Joo
, p. 2993 - 2999 (2007/10/03)
An efficient synthesis of 4-phenylquinolin-2(1H)-one derivatives has been achieved in a one-pot reaction from N-acyl-o-aminobenzophenones 1a-c (a: acyl=acetyl; b: acyl=propanoyl; c: acyl=heptanoyl) using NaH as a base. Treatment of 1 with NaH provided the quinolones 2a-c with 62-83% yields, whereas the reaction in the presence of alkyl iodide (alkyl=methyl, ethyl, n-octyl) gave the corresponding N-alkylated quinolones 3a-g in 75-95% yields. The alkylation reaction of 4-phenylquinolin-2(1H)-one 2a with alkyl halide gave a mixture of N-alkylated and O-alkylated products. Comparison of IR and NMR data of the N-alkylated and O-alkylated compounds with those of 2a-c indicated that 2a-c exist as the lactam form.
Synthesis of 2-alkoxy-4-hydroxy-4-phenyl-3,4-dihydroquinolines, 2-alkoxy-4-phenylquinolines and 2-alkoxy-4-hydroxyquinolines
Hajjem, B.,Efrit, M. L. El,Chihi, A.,Baccar, B.
, p. 330 - 332 (2007/10/02)
Treatment of N-(2-benzoylphenyl or 2-benzoyl-4-chlorophenyl) and N-(2-carbomethoxyphenyl) alkyl imidates 1 and 2 with lithium diisopropylamide (LDA) at -70 deg C affords, respectively, the 2-alkoxy-4-hydroxy-4-phenyl-3,4-dihydroquinolines 3 and the 2-alko
Photochemistry of 2-Phenylbenzothiazole with Ethoxyacetylene and Ethoxypropyne. Synthesis of 1,5-Benzothiazepines
Sindler-Kulyk, M.,Neckers, D. C.
, p. 4914 - 4919 (2007/10/02)
Photocycloaddition reactions of 2-phenylbenzothiazole with electron-rich alkynes, ethoxyacetylene, and ethoxypropyne gave substituted 1,5-benzothiazepines in a one-step processes.
