1159765-59-9Relevant academic research and scientific papers
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.
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.
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
Au(III)-catalyzed regio-and stereoselective tandem synthesis of oxazolo fused naphthyridines and isoquinolines from o-alkynylaldehydes
Jha, Rajeev Ranjan,Danodia, Abhinandan Kumar,Kumar, Sushil,Verma, Akhilesh Kumar
supporting information, p. 610 - 615 (2014/01/23)
An efficient tandem approach for the regio-and stereoselective synthesis of oxazolo-fused naphthyridines 3a-g, 3i-l and isoquinolines 3h, 3m via the reaction of o-alkynylaldehydes 1a-i with chiral amino alcohols 2a-c under mild reaction conditions is described. The stereochemistry and structures of the products were assigned via NOESY and X-ray crystallographic studies.
On water: Silver-catalyzed domino approach for the synthesis of benzoxazine/oxazine-fused isoquinolines and naphthyridines from o-alkynyl aldehydes
Verma, Akhilesh K.,Choudhary, Deepak,Saunthwal, Rakesh K.,Rustagi, Vineeta,Patel, Monika,Tiwari, Rakesh K.
, p. 6657 - 6669 (2013/07/26)
An operationally simple domino approach for the silver-catalyzed synthesis of oxazine/benzoxazine-fused isoquinolines 5a-q and naphthyridines 6a-v by the reaction of o-alkynyl aldehydes 3a-aa with amines having embedded nucleophiles 4a-d under mild reacti
Silver-catalyzed tandem synthesis of naphthyridines and thienopyridines via three-component reaction
Verma, Akhilesh K.,Kotla, Siva K. Reddy,Choudhary, Deepak,Patel, Monika,Tiwari, Rakesh K.
, p. 4386 - 4401 (2013/06/05)
An efficient approach for the silver-catalyzed regioselective tandem synthesis of highly functionalized 1,2-dihydrobenzo[1,6]naphthyridines 6a-z and 7a-e by the reaction of ortho-alkynylaldehydes 3a-n with amines 4a-d and ketones 5a-c/active methylene com
Pyrano[4,3-b]quinolines library generation via iodocyclization and palladium-catalyzed coupling reactions
Aggarwal, Trapti,Imam, Maryam,Kaushik, Naveen K.,Chauhan, Virander S.,Verma, Akhilesh K.
scheme or table, p. 530 - 536 (2011/11/06)
Synthesis of a 80-member library of novel pyrano[4,3-b]quinolines in solution-phase is reported. The key intermediate, 4-iodopyrano[4,3-b]quinolines were synthesized by the electrophilic iodocyclization of corresponding ortho-alkynyl aldehydes in good to
Iodine-catalyzed and solvent-controlled selective electrophilic cyclization and oxidative esterification of ortho-alkynyl aldehydes
Verma, Akhilesh Kumar,Aggarwal, Trapti,Rustagi, Vineeta,Larock, Richard C.
supporting information; experimental part, p. 4064 - 4066 (2010/09/05)
4-Iodo-pyrano[4,3-b]quinolines and ortho-alkynyl esters were synthesized selectively from ortho-alkynyl aldehydes by an iodine-catalyzed and solvent controlled reaction.
Iodine-mediated solvent-controlled selective electrophilic cyclization and oxidative esterification of o-alkynyl aldehydes: An easy access to pyranoquinolines, pyranoquinolinones, and isocumarins
Verma, Akhilesh K.,Rustagi, Vineeta,Aggarwal, Trapti,Singh, Amit P.
scheme or table, p. 7691 - 7703 (2010/12/29)
Chemoselective behavior of iodine in different solvents in the electrophilic iodocyclization of o-alkynyl aldehydes is described. o-Alkynyl aldehydes 3a-t on reaction with I2 in CH2Cl2 with appropriate nucleophiles provides pyrano[4,3-b]quinolines 4a-f, via formation of cyclic iodonium intermediate Q; however, using alcohols as a solvent as well as nucleophile, o-alkynyl esters 5a-y were obtained selectively in good to excellent yields via formation of hypoiodide intermediate R. Subsequently, o-alkynyl esters were converted in to pyranoquinolinones 6a-i and isocoumarin 6j by electrophilic iodocyclization. This developed oxidative esterification provides a novel access for the chemoselective synthesis of esters 5q-u from aldehydes 3n-p without oxidizing primary alcohol present in the substrate.
