16244-23-8Relevant articles and documents
Sulfated Zirconia: An Efficient and Reusable Heterogeneous Catalyst in the Friedel–Crafts Acylation Reaction of 3-Methylindole
Vargas, Darío A.,Méndez, Leticia J.,Cánepa, Alicia S.,Bravo, Rodolfo D.
, p. 1496 - 1502 (2017/08/29)
Abstract: An efficient process for the Friedel–Crafts acylation of 3-methylindole with acid anhydrides in the presence of sulfated zirconia was developed. This catalyst shows excellent catalytic activity with good conversion and selectivity towards formation of the products of 2-acylation (3-methyl-1H-indol-2-yl)ketones. Other advantages related to this process are the simple work-up procedure and smaller production of chemical waste. The catalyst was easily recycled and reused with a minimal loss in activity through three reaction cycles. The catalyst was characterized by FT-IR spectroscopy, X-Ray diffraction and superficial acidity. Graphical Abstract: [Figure not available: see fulltext.].
Mechanistic Insights into the Radical S-adenosyl- l -methionine Enzyme NosL from a Substrate Analogue and the Shunt Products
Ji, Xinjian,Li, Yongzhen,Jia, Youli,Ding, Wei,Zhang, Qi
supporting information, p. 3334 - 3337 (2016/03/22)
The radical S-adenosyl-l-methionine (SAM) enzyme NosL catalyzes the transformation of l-tryptophan into 3-methyl-2-indolic acid (MIA), which is a key intermediate in the biosynthesis of a clinically interesting antibiotic nosiheptide. NosL catalysis was i
Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines
Giles, Robert G.,Heaney, Harry,Plater, M. John
, p. 7367 - 7385 (2015/08/24)
Abstract Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basification and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.
Cyclocondensation reactions between 2-acyl-3-indoleacetic acid derivatives and phenylglycinol: Enantioselective synthesis of 1-substituted tetrahydro-β-carboline alkaloids
Amat, Mercedes,Subrizi, Fabiana,Elias, Viviane,Llor, Nuria,Molins, Elies,Bosch, Joan
scheme or table, p. 1835 - 1842 (2012/05/05)
Cyclocondensation reactions between a variety of 2-acyl-3-indoleacetic acid derivatives and (R)-phenylglycinol were studied. Successful results were obtained from N-alkyl keto acid derivatives. The resulting tetracyclic lactams provide straightforward access to enantiopure 1-substituted tetrahydro-β- carboline alkaloids.
Synthesis and self-association of double-helical AADD arrays
Mudraboyina, Bhanu P.,Wisner, James A.
supporting information, p. 14157 - 14164 (2013/01/15)
The design and syntheses of four self-complementary oligomers that contain an underlying AADD hydrogen bond sequence are presented, and their self-association was examined in the solution and solid state. The molecular recognition between the two strands
Minimal complementary hydrogen-bonded double helices
Wang, Hong-Bo,Mudraboyina, Bhanu P.,Li, Jiaxin,Wisner, James A.
supporting information; experimental part, p. 7343 - 7345 (2010/11/05)
Molecular strands incorporating three hydrogen bond donor (D) or acceptor (A) heterocycles form highly stable double helical complexes through a complementary AAA-DDD array structure.
A Direct Access to 3-(2-Oxoalkyl)indoles via Aluminum Chloride Induced C-C Bond Formation
Pal, Manojit,Dakarapu, Rambabu,Padakanti, Srinivas
, p. 2913 - 2916 (2007/10/03)
3-Methylindole is acylated regioselectively at the methyl group when treated with a variety of acyl chlorides in 1,2-dichloroethane in the presence of AlCl3, affording a mild and direct method for the synthesis of 3-(2-oxoalkyl)-indoles. The product formation in this one-pot reaction largely depends on the conditions of the reaction employed. The methodology does not require protection-deprotection steps and is amenable for the scale-up synthesis of these indole derivatives.
Diels-Alder reaction of pyrano[3,4-b]indolones with an electron- deficient pyridazinone: A new pathway to carbazole-fused pyridazines
Haider, Norbert,Kaeferboeck, Johann,Matyus, Peter
, p. 2703 - 2710 (2007/10/03)
Thermally induced [4+2] cycloaddition reactions of 5-ethanesulfonyl-2- methylpyridazin-3(2H)-one (2) with pyrano[3,4-b]indol-3(9H)-ones (1, 4) affords isomeric pyridazino[4,5-b]carbazolones (3a,b, 5a,b), the product ratio depending on the substitution pattern of the diene. Two carbazolocarbazoles (6, 7) were obtained as side products.
Synthesis of 1,9-dimethyl-9H-pyrrolo[1,2-a]indole and its lithium salt
Kisun'ko,Kisun'ko,Brusova,Lemenovskii
, p. 727 - 729 (2007/10/03)
1,9-Dimethyl-9H-pyrrolo[1,2-a]indole was synthesized by reaction of triphenyl(vinyl)phosphonium bromide with 2-acetyl-3-methylindole sodium salt. Treatment of 1,9-dimethyl-9H-pyrrolo[1,2-a]indole with a solution of n-butyllithium in hexane gave the corresponding lithium salt in quantitative yield.
Metal Reagents in Organic Reactions. Part-VI 1,2. Oxidation of Indoles with Thallium(III) Acetate
Banerji, Avijit,Ray, Rita,Pal, Sudhir C.,Banerji, Debasis,Maiti, Kaustabh K.
, p. 698 - 704 (2007/10/03)
The action of thallium(III) acetate on a number of indoles, differently substituted in the 2- and 3-positions, has been investigated. Monomeric and 'dimeric' oxidation products are obtained; the structures of the products depend on the substituents present in the substrate. A novel oxidative dimerisation of 2,3-disubstituted indoles to indolo[3,2-b]carbazoles is observed. The generation of the products could be rationalised by the initial formation of an unstable, non-isolable 3-thallated-indolenine derivative.
