868765-12-2Relevant articles and documents
Light-Enabled Radical 1,4-Aryl Migration Via a Phospho-Smiles Rearrangement
De Abreu, Maxime,Belmont, Philippe,Brachet, Etienne
, p. 3758 - 3767 (2021/02/01)
Rearrangement reactions in organic chemistry are attractive strategies to build efficiently complex scaffolds, in just one step, from simple starting materials. Among them, aryl migrations are certainly one of the most useful and straightforward rearrangement for building attractive carbon-carbon bonds. Of note, anionic aryl migration reactions have been largely described compared to their radical counterparts. Recently, visible-light catalysis has proven its efficiency to generate such radical rearrangements due to the concomitant loss of a particle (often CO2 or SO2), which is the driving-force of the reaction. Here, we disclose a Smiles-type rearrangement, triggered by a phosphorus-containing unit (arylphosphoramidate), therefore called "phospho-Smiles"rearrangement, allowing a Csp2-Csp2 bond formation thanks to a 1,4-aryl migration reaction. In addition, combining this approach with a radical hydroamination/amination reaction produces an amination/phospho-Smiles cascade particularly attractive, for instance, to investigate the synthesis of the phthalazine core, a scarcely described scaffold of interest for medicinal chemistry projects.
Tandem 6π-Azatriene Electrocyclization of Fused Amino-cyclopentenones: Synthesis of Functionalized Pyrrolo- And Indolo-quinoxalines
Saini, Kapil Mohan,Saunthwal, Rakesh K.,Kumar, Ankit,Verma, Akhilesh K.
supporting information, p. 7586 - 7591 (2021/10/12)
A tandem 6π-azacyclization approach for the synthesis of diversified pyrrolo/indolo[1,2-a]quinoxalines from amino-cyclopentenones has been developed. The reaction proceeds through a trifluoroacetic-acid-mediated 6π-electrocyclization and concomitant opening of the cyclopentenone ring. The advantageous features of the developed chemistry include transition-metal-free conditions, operational simplicity, and a broad substrate scope. Further X-ray crystallographic studies confirm the assigned structures of the fused heterocycles.
Transition-metal-free oxidative cyclization reaction of enynals to access pyrane-2-one derivatives
Abbasi Kejani, Alireza,Ansari, Farzaneh,Armaghan, Mahsa,Balalaie, Saeed,Frank, Walter,Jafarpour, Farnaz,Khosravi, Hormoz
, p. 4263 - 4267 (2021/05/31)
A novel and efficient metal-free C-H functionalization of enynals is developed to synthesize α-pyrone derivatives via the formation of two C-O bonds. In this project, K2S2O8 has been introduced as an efficient oxygen source and C-H functionalization agent in regioselective oxidative cyclization reaction with a relatively broad substrate scope.
Na2S·9H2O mediated facile synthesis of 1,3-dihydrofuro[3,4-b]quinoline derivatives via domino reduction approach
Singh, Rashmi,Gupta, Tanu,Sharma, Vishal Prasad,Singh, Radhey M.,Tewari, Ashish Kumar
supporting information, (2021/09/22)
A simple, highly efficient method for synthesis of 1,3-dihydrofuro[3,4-b]quinoline is described by the reaction of o-arylalkynyl quinoline aldehydes with Na2S·9H2O via domino reduction approach. The method is simple and proceeds under mild condition under an air atmosphere to give 1,3-dihydrofuro[3,4-b]quinoline in good to excellent yields. The beauty of the reaction is cyclization as well as reduction has been taken place in the same reaction pot. Also the conversion of aldehyde into primary alcohol has been discussed under the same reaction condition.
Synthesis of cyclopentaquinolinone and cyclopentapyridinone from: Ortho-alkynyl-N-arylaldehyde via superbase-promoted C-N, C-O and C-C bond formation
Saini, Kapil Mohan,Saunthwal, Rakesh K.,Sushmita,Verma, Akhilesh K.
supporting information, p. 5594 - 5601 (2020/08/21)
An environmentally benign, transition metal-free, superbase-mediated intramolecular annulation of o-alkynylaldehydes with primary amines forms highly functionalized amino-substituted cyclopentaquinolinones and cyclopentapyridinones via C-N, C-C, and CO bond formation. Contrary to the traditional approaches of ring closures, a different mode of annulation is disclosed. The protocol involves the in situ generations of imine intermediate followed by potassium hydroxide-promoted intramolecular cyclization and subsequent dimethyl sulfoxide induced dehydrogenation leads to the formation of N-heterocycles. X-ray crystallographic studies support the assigned structures of the amino-fused N-heterocycles.
Catalytic formal [4 + 1] isocyanide-based cycloaddition: An efficient strategy for the synthesis of 1: H -cyclopenta [b] quinolin-1-one derivatives
Motaghi, Milad,Khosravi, Hormoz,Balalaie, Saeed,Rominger, Frank
, p. 275 - 282 (2019/01/10)
An unprecedented catalytic isocyanide-based cycloaddition of alkyl and aryl isocyanides with (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes was developed for the direct and efficient synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives. On the
Iodine mediated: In situ generation of R-Se-I: Application towards the construction of pyrano[4,3- b] quinoline heterocycles and fluorescence properties
Win, Khin Myat Noe,Sonawane, Amol D.,Koketsu, Mamoru
supporting information, p. 9039 - 9049 (2019/10/28)
In this paper, we report the iodine mediated in situ generation of R-Se-I and further its application towards the construction of pyrano[4,3-b]quinolin-1-one derivatives. The structural elaboration of 1-chloro-8-methyl-3-phenylbenzo[b][1,6]naphthyridine 6 was successfully achieved by Sonogashira, Suzuki coupling and dehalogenation reactions. Finally, the synthesized compounds 4a, 5a, 5b, 6, and 7a-7c were studied for photophysical properties including UV-absorption, fluorescence, and quantum yield studies. The synthesized pyranoquinoline derivatives showed λmax, Fmax and Φf values in the range of 391-447 nm, 436-486 nm and 0.004-0.301, respectively in chloroform solvent.
Silver-Catalyzed Domino Hydroarylation/Cycloisomerization Reactions of 2-Alkynylquinoline-3-carbaldehydes: Access to (Hetero)arylpyranoquinolines
Bontemps, Alexis,Mariaule, Ga?lle,Desbène-Finck, Stéphanie,Helissey, Philippe,Giorgi-Renault, Sylviane,Michelet, Véronique,Belmont, Philippe
, p. 2178 - 2190 (2016/07/15)
A silver trifluoromethanesulfonate catalyzed efficient access to the indolylpyranoquinoline scaffold is reported. Starting from 2-alkynylquinoline-3-carbaldehyde units with various substitution patterns on the quinoline and alkynyl parts, the use of silver trifluoromethanesulfonate (10 mol%) in 1,2-dichloroethane allowed a domino hydroarylation/cycloisomerization reaction, generating (hetero)aryl-functionalized pyranoquinolines. The heteroarenes that were used are N-methylindole (18 compounds, 67-100%), indole, and 2-methylindole (4 compounds, 36-89%), and the reaction was also compatible to a lesser extent with arenes such as pyrroles (5 compounds, 43-90%), 1,3,5-trimethoxybenzene, and 3-methylbenzofuran.
FeCl3·6H2O-catalyzed facile and efficient synthesis of pyrano[4,3-b]quinolines and isochromenes
Asthana, Mrityunjaya,Singh, Jay Bahadur,Singh, Radhey M.
, p. 615 - 618 (2016/01/20)
An inexpensive 1 mol % FeCl3·6H2O reagent has been developed for the synthesis of 1,3-disubstituted 1H-pyrano[4,3-b]quinolines from o-arylethnylquinonylmethanol via 6-endo-dig cyclization of alcoholic -OH onto alkynes in good to excellent yields. The reaction conditions were successfully exploited on primary and tertiary alcohol analogs. The reagent was further generalized with the aromatic alcohol analogs providing the synthesis of isochromenes in good yields. The enhancement in the reaction rates and yields from primary to secondary to tertiary alcohols could be attributed to inductive effect of alkyl groups which enhanced the nucleophilicity of hydroxyl group and accelerated the cyclization mode.
Efficient synthesis via azide-alkyne Huisgen [3+2] cycloaddition reaction and antifungal activity studies of novel triazoloquinolines
Saravanan, Nagarajan,Arthanareeswari, Maruthapillai,Kamaraj, Palanisamy,Sivakumar, Bitragunta
, p. 5379 - 5388 (2015/07/08)
New functionalized 1,2,3-triazoloquinolines were achieved by intramolecular azide-alkyne Huisgen [3+2] cycloaddition. These derivatives were synthesized via the key Baylis-Hillman adduct under mild, neutral conditions in short duration and consistently go
