19069-76-2Relevant academic research and scientific papers
Efficient two-step synthesis of structurally diverse indolo[2,3-: B] quinoline derivatives
Kundal, Sandip,Chakraborty, Baitan,Paul, Kartick,Jana, Umasish
, p. 2321 - 2325 (2019)
A general and efficient synthesis of diverse tetracyclic indolo[2,3-b]quinoline derivatives was achieved through palladium-catalyzed domino carboannulation/cross-coupling and DDQ-mediated double cross-dehydrogenative C-N bond formation. This approach provides a straightforward, atom-economical and concise route to easily access a diverse range of tetracyclic indolo[2,3-b]quinolines and their analogues in excellent yields with good tolerance of functional groups.
Domino N2-Extrusion-Cyclization of Alkynylarylketone Derivatives for the Synthesis of Indoloquinolines and Carbocycle-Fused Quinolines
Akkachairin, Bhornrawin,Tummatorn, Jumreang,Khamsuwan, Narumol,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
, p. 11254 - 11268 (2018/09/06)
New synthetic approaches for the synthesis of indoloquinolines and carbocycle-fused quinolines have been developed employing alkynylketone substrates. These synthetic transformations involved the application of N2-extrusion of azido complexes as a key step to generate carbodiimidium ion and nitrilium ion in situ, which further cyclized intramolecularly with alkyne via a domino process to provide indoloquinolines and carbocycle-fused quinolines, respectively, in moderate to good yields.
Microwave-Assisted Cascade Strategy for the Synthesis of Indolo[2,3-b]quinolines from 2-(Phenylethynyl)anilines and Aryl Isothiocynates
Ali, Wajid,Dahiya, Anjali,Pandey, Ramdhari,Alam, Tipu,Patel, Bhisma K.
supporting information, p. 2089 - 2096 (2017/02/26)
The in situ generated o-alkynylthioureas obtain by reacting 2-(phenylethynyl)anilines and aryl isothiocynates undergo efficient cascade cyclization in the presence of Ag2CO3 to form indoloquinolines under microwave heating. The prese
An efficient iron-promoted synthesis of 6H-indolo[2,3- b] quinolines and neocryptolepine derivatives
Yan, Zicong,Wan, Changfeng,Wan, Jianyong,Wang, Zhiyong
, p. 4405 - 4408 (2016/06/06)
A facile and practical method for the preparation of 6H-indolo[2,3-b]quinolines and neocryptolepines was developed under the promotion of the easily available ferric trichloride, affording the desired products with moderate to good yields.
A concise formal synthesis of alkaloid cryptotackiene and substituted 6H-indolo[2,3-b]quimolines
Sundaram,Venkatesh,Syam Kumart,Ila,Junjappa
, p. 5760 - 5762 (2007/10/03)
A five-step formal synthesis of alkaloid cryptotackiene and its 2-formyl, 11-methyyphenyl derivatives involving conjugate addition of enolate anion from cyclohexanone (or 4-methylcyclohexanone) to bis[(methylsulfanyl)-methylene] -2-oxindole followed by heterocyclization in the presence of ammonium acetate as the key step has been developed. The 11-methylsulfanyl group in the initial precursor can be either desulfurized (Raney Ni) or replaced by methyl/phenyl groups via nickel-catalyzed cross-coupling reaction with appropriate Grignard reagents.
Synthesis of carbocyclic and heterocyclic fused quinolines by cascade radical annulations of unsaturated N-aryl thiocarbamates, thioamides, and thioureas.
Du,Curran, Dennis P
, p. 1765 - 1768 (2007/10/03)
[reaction: see text] Tandem radical cyclizations of suitably substituted N-aryl thiocarbamates, thioamides, and thioureas are induced by exposure to tris(trimethylsilyl)silane (TTMSH) and UV light and provide furoquinolines, isofuroquinolines, cyclopentaq
Biradicals from thermolysis of N-[2-(1-alkynyl)phenyl]-N'- phenylcarbodiimides and their subsequent transformations to 6H-indolo[2,3- b]quinolines
Shi, Chongsheng,Zhang, Quan,Wang, Kung K.
, p. 925 - 932 (2007/10/03)
Thermolysis of the carbodiimide 9a in γ-terpinene at 138 °C produced 2-(phenylamino)quinoline (11a, 49%) and the parent 6H-indolo[2,3-b]quinoline (14a, 16%). Apparently, 11a was produced via the biradical 10a followed by hydrogen-atom abstraction from γ-terpinene. A two-step biradical pathway through 12a or a one-step intramolecular Diels-Alder reaction could furnish 13a, which then underwent tautomerization to give 14a. With the carbodiimide 9b having a trimethylsilyl substituent at the acetylenic terminus, thermolysis in refluxing p-xylene at 138 °C produced the 6H-indolo[2,3- b]quinoline 14b (86%) exclusively. Treatment of 14b with 6 N NaOH in refluxing ethanol then furnished 14a in 92% yield. Similarly, the 6H- indolo[2,3-b]quinolines 14c-f were obtained from thermolysis of the carbodiimides 9c-f. The use of the aza-Wittig reaction between 4- methoxyphenyl isocyanate and the iminophosphoranes 2d and 2f to produce the corresponding carbodiimides followed by thermolysis furnished the 6H- indolo[2,3-b]quinolines 16d and 16f having a methoxy substituent at the C-2 position. Thermolysis of the carbodiimides 25a and 25b produced 26a and 26b having two indoloquinoline units connected at the 11 and 11' positions with either a three-carbon or a five-carbon tether. Using 1,4-phenylene diisocyanate for the aza-Wittig reaction with 2 equiv of the iminophosphorane 2g followed by thermolysis furnished 31 (66%) having two indoloquinoline units incorporated in the seven fused rings.
