13622-59-8Relevant academic research and scientific papers
Heumann indole flow chemistry process
Crifar, Cynthia,Dücker, Fenja L.,Nguyen Thanh, Sacha,Kairouz, Vanessa,Lubell, William D.
, p. 10929 - 10937 (2019)
Continuous flow chemistry has improved efficiency in the Heumann indole process. 3-Substituted indoles were prepared by three flow steps performed in succession in better overall yield and shorter reaction times relative to their batch counterparts. Novel
Unexpected Insertion of Nitrogen into a C-C Bond: Access to 2,3-Disubstituted Quinazolinone Scaffolds
Liu, Hui-Li,Li, Xiao-Tong,Tian, Heng-Zhi,Sun, Xing-Wen
, p. 4579 - 4583 (2021)
A novel, practical, highly efficient, and transition metal free nitrogen insertion reaction for the synthesis of 2,3-disubstituted quinazolinone derivatives was developed. Diverse functionalized 3-indolinone-2-carboxylates and nitrosoarenes with a wide range of substituted nitrosobenzenes, nitrosopyridines, dibenzofuranyl, or dibenzothienyl nitroso compounds worked smoothly to give 2,3-disubstituted quinazolinone derivatives in good to excellent yields (69-98%). A gram-scale reaction was achieved, and an afloqualone analogue was synthesized under the mild reaction conditions.
Improved scalable synthesis and biological activity of “indoxyl-gal,” a chromogenic histochemical used for the identification of lac+ organisms
Banasik, Brent,Mai, Tam,Samadpour, Mansour
supporting information, p. 822 - 825 (2018/11/06)
An improved and operationally simple synthesis of 3-indoxyl-β-D-galactopyranoside (in-doxyl-gal) is disclosed. Indoxyl-gal is a sensitive chromogenic histochemical used for the identification of β-galactosidase enzymatic activity (lacZ gene). Synthesis of indoxyl-gal is improved to 25% overall yield in 5 linear steps from affordable starting materials with minimal chromatography. Biological testing confirmed the detection of β-galactosidase activity in all (100%, 19 strains) coliform bacteria using membrane filtration and modified MI agar.
Stereogenic: Cis -2-substituted- N -acetyl-3-hydroxy-indolines via ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation
Luo, Zhonghua,Sun, Guodong,Zhou, Zihong,Liu, Guozhu,Luan, Baolei,Lin, Yicao,Zhang, Lei,Wang, Zhongqing
supporting information, p. 13503 - 13506 (2018/12/12)
Ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation of racemic 2-substituted-N-acetyl-3-oxoindolines to cis-2-substituted-N-acetyl-3-hydroxyindolines is reported. Using the homochiral {Ru[TfDPEN](p-cymene)} catalyst with S/C = 400 in a HCO2H/Et3N mixture, up to >99.9% ee and >99:1 dr are obtained with high yields (79-98%). This method provides the first example of preparing enantiomerically pure indolines through asymmetric transfer hydrogenation (ATH).
Organocatalytic enantioselective amination of 2-substituted indolin-3-ones: A strategy for the synthesis of chiral α-hydrazino esters
Yarlagadda, Suresh,Ramesh,Ravikumar Reddy,Srinivas,Sridhar,Subba Reddy
supporting information, p. 170 - 173 (2017/11/27)
An efficient enantioselective α-amination of 2-substituted 3-indolinones has been achieved for the first time using hydroquinidine as a chiral catalyst through an aza-Michael reaction. The desired α-hydrazino esters are obtained in excellent yields with h
Organocatalytic asymmetric Michael-Michael cascade for the construction of highly functionalized N-fused piperidinoindoline derivatives
Zhao, Yong-Long,Wang, Yao,Cao, Jian,Liang, Yong-Min,Xu, Peng-Fei
supporting information, p. 2438 - 2441 (2014/05/20)
Application of indolin-3-one derivatives in a cascade reaction for efficient assembly of complex molecules is a much less explored research area. It is demonstrated that structurally interesting polysubstituted piperidino[1,2-a]indoline compounds containi
Oxidative coupling of indoles with 3-oxindoles
Jessing, Mikkel,Baran, Phil S.
experimental part, p. 1739 - 1745 (2011/05/05)
A mild procedure for the union of 3-oxindoles with indoles is reported using oxidative coupling. : The Japan Institute of Heterocyclic Chemistry.
Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARγ partial agonists
Dropinski, James F.,Akiyama, Taro,Einstein, Monica,Habulihaz, Bahanu,Doebber, Tom,Berger, Joel P.,Meinke, Peter T.,Shi, Guo Q.
, p. 5035 - 5038 (2007/10/03)
A series of novel aryl indole-2-carboxylic acids has been identified as potent selective PPARγ modulators. Their chemical synthesis and in vitro activities are discussed. Compound 5 was selected for in vivo testing in the db/db mouse model of type 2 diabetes and resulted in reduction of hyperglycemia at comparable plasma exposure when compared to rosiglitazone.
3-substituted indole antiproliferative angiogenesis inhibitors
-
, (2008/06/13)
3-Substituted indole carbohydrazides having the formula are useful for inhibiting angiogenesis and cell proliferation. Also disclosed are compositions which inhibit angiogenesis and cell proliferation and methods of inhibiting angiogenesis and cancer in a mammal.
Quinazoline Carboxylic Acids, V: 1,4-Dihydro-quinazoline-4-on-1-yl-acetic Acids and Esters
Suesse, Manfred,Johne, Siegfried
, p. 499 - 510 (2007/10/02)
1,4-Dihydro-quinazoline-4-on-1-yl-acetic acids 5 were prepared by reaction of 3,1-benzoxazine-2,4-diones 1 with ammonia to 2.Cyclisation of 2 gave 4 and their hydrolysis lead to 5. 2-Substituted quinazolinones 9 could be obtained by reaction of 2 with aci
