17276-85-6Relevant academic research and scientific papers
An improved synthesis of α-carbolines under microwave irradiation
Vera-Luque, Patricia,Alajarin, Ramon,Alvarez-Builla, Julio,Vaquero, Juan J.
, p. 415 - 418 (2006)
α-Carbolines are interesting core structures for designing DNA-interacting small molecules. However, these compounds are not commercially available and their synthetic methods are low yielding or time consuming. The shortest synthetic route, the modified Graebe-Ullmann reaction, has been optimized by using microwave heating in four different types of apparatus to give shorter reaction times and enhanced yields. Optimized conditions enabled the preparation of a small library of α-carbolines.
Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization
Das, Sandip Kumar,Roy, Satyajit,Khatua, Hillol,Chattopadhyay, Buddhadeb
supporting information, p. 8429 - 8433 (2018/07/09)
An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.
A 9H-pyrido [2,3-b] indoles the synthetic method of the compound of
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Paragraph 0012; 0045; 0046; 0047, (2017/01/02)
The invention discloses a synthesis method of 9H-pyridino[2,3-b]indole compounds, belonging to the technical field of organic synthesis. The technical scheme is as follows: the synthesis method comprises the following steps: dissolving 1-bromo-2-(2,2-dibromovinyl)benzene or derivatives thereof, ammonia water and alpha,beta-unsaturated aldehyde compounds in an organic solvent, adding a catalyst transition metal salt and an additive, and reacting at 60-100 DEG C in the presence of air to obtain the 9H-pyridino[2,3-b]indole compounds. The synthesis process is one-pot multicomponent series reaction, is simple to operate, avoids waste of resources and environmental pollution caused by the use of multiple reagents in multiple reaction steps, the purification treatment on the intermediate in each reaction step and the like, and provides an economical, practical, green and environment-friendly novel method for synthesizing the 9H-pyridino[2,3-b]indole compounds.
Selective access to 3-cyano-1 H -indoles, 9 H -pyrimido[4,5- b ]indoles, or 9 H -Pyrido[2,3- b ]indoles through copper-catalyzed one-pot multicomponent cascade reactions
Li, Bin,Guo, Shenghai,Zhang, Ju,Zhang, Xinying,Fan, Xuesen
, p. 5444 - 5456 (2015/06/16)
Novel and selective synthetic approaches toward indole derivatives via copper-catalyzed one-pot multicomponent cascade reactions of 1-bromo-2-(2,2-dibromovinyl)benzenes with aldehydes and aqueous ammonia are presented. Intriguingly, the concentration of a
A new route to α-carbolines based on 6π-electrocyclization of indole-3-alkenyl oximes
Markey, Sophie J.,Lewis, William,Moody, Christopher J.
, p. 6306 - 6308 (2014/01/17)
Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 C under microwave irradiation undergo loss of the Boc-group, and 6π-electrocyclization to α-carbolines, following aromatization by loss of methanol (11 examples, 30-90% yield).
Thermal rearrangement of indolyl oxime esters to pyridoindoles
Portela-Cubillo, Fernando,Surgenor, Brian A.,Aitken, R. Alan,Walton, John C.
, p. 8124 - 8127 (2008/12/22)
(Chemical Equation Presented) Acyl oximes derived from a variety of indolylalkanones underwent a ring closure sequence during FVP to afford 9H-pyrido[2,3-b]indoles. Unlike UV light promoted reactions of oxime esters, the mechanism is almost certainly not mediated by iminyl radicals but probably involves tautomerism, elimination of acetic acid, and a final electrocyclic ring closure.
Microwave-assisted syntheses of N-heterocycles using alkenone-, alkynone- and aryl-carbonyl O-phenyl oximes: Formal synthesis of neocryptolepine
Portela-Cubillo, Fernando,Scott, Jackie S.,Walton, John C.
, p. 5558 - 5565 (2008/12/20)
(Chemical Equation Presented) This research aimed to provide a new and "clean" synthetic method that would enable both known and novel N-heterocycles to be prepared efficiently. O-Phenyl oximes were found to be excellent precursors for iminyl radicals with a variety of acceptor side chains. Dihyropyrroles were made in good yields from O-phenyl oximes containing pent-4-ene acceptors. The analogous process with a hex-5-enyl acceptor did not yield a dihydropyridine, probably because the 6-exo-trig ring closure of the iminyl radical was too slow to compete with H-atom abstraction. The iminyl radical from a precursor with a pent-4-yne type side chain underwent ring closure followed by rearrangement to afford a pyrrole derivative. Suitably substituted iminyl radicals ring closed readily onto aromatic acceptors, thus enabling several polycyclic systems to be accessed. Quinolines were made from 3-phenylpropanones via their O-phenyl oximes. Syntheses of phenanthridines starting from 2-formylbiphenyls were particularly efficient, and this approach enabled the natural product trisphaeridine to be made. Starting from 2-phenylnicotinaldehyde derivatives, ring closures of the derived iminyl radicals onto the phenyl rings yielded benzo[h][1,6]naphthyridines. Similarly, ring closure onto a phenyl ring from a benzothiophene-based iminyl yielded a benzo[b-]thieno[2,3-c]quinoline. By way of contrast, iminyl radical ring closure onto pyridine rings was not observed. However, iminyl radicals did cyclize onto indoles, enabling indolopyridines to be prepared. The latter route was exploited in a short formal synthesis of neocryptolepine starting from 2-((1H-indol-3-yl)methyl)cyclohexanone.
Microwave-assisted preparations of dihydropyrroles from alkenone O-phenyl oximes
Portela-Cubillo, Fernando,Scott, Jackie S.,Walton, John C.
, p. 4041 - 4043 (2008/03/14)
Microwave irradiation of alkenone O-phenyl oximes produces iminyl radicals that ring close to yield dihydropyrrole derivatives; pyrroles and pyridines can be obtained from related precursors. The Royal Society of Chemistry.
Synthesis of α-carbolines by copper-catalyzed radical cyclization of β-(3-indolyl) ketone O-pentafluorobenzoyloximes
Tanaka, Kenichi,Kitamura, Mitsuru,Narasaka, Koichi
, p. 1659 - 1664 (2007/10/03)
Radical cyclization of β-(3-indolyl) ketone O-pentafluorobenzoyloximes proceeds by the treatment with a catalytic amount of copper powder in 1,2-dichloroethane to generate 3,4-dihydro-α-carbolines, which are oxidized to α-carbolines with chloranil.
Synthesis of α-carbolines from β-(3-indolyl) ketone 0-2,4-dinitrophenyloximes
Ono, Ayako,Narasaka, Koichi
, p. 146 - 147 (2007/10/03)
α-Carbolines are synthesized from β-(3-indolyl) ketone O-2,4-dinitrophenyloximes by the treatment with sodium hydride and sodium cyanoborohydride.
