243-38-9Relevant academic research and scientific papers
Ruthenium-exchanged FAU-Y zeolite catalyzed improvement in the synthesis of 6H-indolo[2,3-b]quinolines
Khorshidi, Alireza,Tabatabaeian, Khalil
, p. 128 - 131 (2011)
Ruthenium-exchanged FAU-Y zeolite (RuY) was used as a recyclable catalyst for preparation of 6H-indolo[2,3-b]quinolines from the reaction of indole-3-carbaldehyde with aryl amines in refluxing dioxane. Under the above mentioned conditions, reasonable yields of the desired products with different substituents on the quinoline ring were obtained.
Microwave-induced bismuth(III)-catalyzed synthesis of linear indoloquinolines
Parvatkar, Prakash T.,Parameswaran,Bandyopadhyay, Debasish,Mukherjee, Sanghamitra,Banik, Bimal K.
, p. 2948 - 2951 (2017)
Microwave-induced Bi(NO3)3-catalyzed one-pot synthesis of a series of linear indoloquinolines is accomplished under mild reaction conditions. While majority of these examples were carried out under solvent-free conditions, in a few cases, minimal quantity of THF is used as solvent. The methodology involves several unique reaction pathways, providing different linear indolo[2,3-b]quinolines in good yields from readily available starting materials and using environmentally benign Bi(NO3)3·5H2O as catalyst.
An Alternate Synthesis of 6H-Indolo[2,3-b]quinoline via One-Pot Alkylation–Dehydration–Cyclization–Aromatization Approach
Kadam, Hari K.,Tilve, Santosh G.
, p. 2066 - 2069 (2016)
A simple, straightforward and efficient synthesis of 6H-indolo[2,3-b]quinoline, a natural product isolated from leaves of Justicia betonica, is achieved through a pivalic acid-assisted one-pot alkylation–dehydration–cyclization–aromatization approach. This synthesis constitutes a formal approach toward a biologically important alkaloid neocryptolepine.
N-Bromosuccinimide as an efficient catalyst for the synthesis of indolo[2,3-b]quinolines
Ghorbani-Vaghei, Ramin,Malaekehpoor, Seyedeh Mina
, p. 4751 - 4753 (2012)
The use of N-bromosuccinimide as a catalyst promoted the synthesis of polycyclic indolo[2,3-b]quinoline derivatives in good to high yields in the reactions of various aryl amines with indole-3-carbaldehyde at room temperature under mild conditions.
Access to Structurally Diverse Quinoline-Fused Heterocycles via Rhodium(III)-Catalyzed C-C/C-N Coupling of Bifunctional Substrates
Yu, Songjie,Li, Yunyun,Zhou, Xukai,Wang, He,Kong, Lingheng,Li, Xingwei
, p. 2812 - 2815 (2016)
Rhodium(III)-catalyzed C-H activation of heteroarenes and functionalization with bifunctional substrates such as anthranils allows facile construction of quinoline-fused heterocycles under redox-neutral conditions. The couplings feature broad substrate scope and provide step-economical access to two classes of quinoline-fused condensed heterocycles.
Tandem Rh(III)-Catalyzed C-H Amination/Annulation Reactions: Synthesis of Indoloquinoline Derivatives in Water
Shi, Liangliang,Wang, Baiquan
, p. 2820 - 2823 (2016)
An efficient Rh(III)-catalyzed synthetic method for indoloquinoline derivatives from readily available indoles and isoxazoles was developed. This annulation procedure undergoes tandem C-H activation, cyclization, and condensation steps. In this domino cyclization reaction, water is an efficient solvent. A catalytically competent five-membered rhodacycle has been isolated and characterized, thus revealing a key intermediate in the catalytic cycle.
Formal total synthesis of the alkaloid cryptotackieine (neocryptolepine)
Alajarin,Molina,Vidal
, p. 747 - 748 (1997)
A straightforward synthesis of quinindoline (4), the immediate chemical precursor of the alkaloid cryptotackieine (neocryptolepine) (1), is described.
Synthetic studies towards benzofuro[2,3-b]quinoline and 6H-indolo[2,3-b]quinoline cores: Total synthesis of norneocryptolepine and neocryptolepine
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Arutyunov, Nikolai A.,Gasanova, Amina Z.,Lower, Carolyn,Rubin, Michael
, (2021/09/14)
An innovative acid-assisted cascade transformation of indoles with 2-nitrostyrenes was developed, allowing for the one-pot assembly of heterocyclic scaffolds with four fused rings. This strategy was subsequently employed for the concise total synthesis of two natural products, the alkaloids norneocryptolepine and neocryptolepine.
Synthesis and evaluation of the tetracyclic ring-system of isocryptolepine and regioiso-mers for antimalarial, antiproliferative and antimicrobial activities
Albrigtsen, Marte,Andersen, Jeanette H.,Avery, Vicky M.,H?heim, Katja S.,Helgeland, Ida T. Urdal,Kennedy, Emily K.,Lauga, Clémence,Lindb?ck, Emil,Matringe, Théodora,Sydnes, Magne O.,Tan, Kah Ni
, (2021/06/16)
A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 μM; 9b: MBIC = 100 μM).
Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles
Roy, Subhra Kanti,Purkait, Anisha,Aziz, Sk Md Tarik,Jana, Chandan K.
supporting information, p. 3167 - 3170 (2020/03/23)
Traditionally, amines react with nitrosoarenes to provide the corresponding imines or azo compounds. Herein, we report an acid mediated annulation reaction of aliphatic amines and nitrosoarenes to provide indole derivatives. The elusive direct annulation of aliphatic amines and nitrosoarenes via simultaneous C-C and C-N bond formation was achieved under metal free conditions. This conceptually novel method for indole synthesis does not require pre-functionalization steps for the new C-C and C-N bond formation. The method has been applied for an elegant synthesis of nor-neocryptolepine and neocryptolepine.
