A simple and efficient synthesis of 11H-pyrido[2,1-b]quinazolin-11-ones by Cu(OAc)2·H2O-catalyzed reaction of easily available substituted isatins and 2-bromopyridine derivatives has been developed. The reaction involves C-N/C-C bond cleavage and two C-N bond formations in a one-pot operation. This methodology is complementary to previously reported synthetic procedures, and two plausible reaction mechanisms are discussed.
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http://dx.doi.org/10.1021/acs.orglett.6b00113 | DOI Listing |
Org Biomol Chem
June 2021
Faculty of Chemical Engineering, Ho Chi Minh City University of Technology (HCMUT), 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam. and Vietnam National University Ho Chi Minh City, Linh Trung Ward, Thu Duc District, Ho Chi Minh City, Vietnam.
Pyrido-fused quinazolinones were synthesized via copper-catalyzed cascade C(sp2)-H amination and annulation of 2-aminoarylmethanols with isoquinolines or pyridines. The transformation proceeded readily in the presence of a commercially available CuCl2 catalyst with molecular oxygen as a green oxidant. Moreover, the dehydrogenative cross-coupling of 2-aminoarylmethanols with tetrahydroisoquinolines was explored, in which CuBr exhibited higher catalytic activity than CuCl2.
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October 2020
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
Two isomeric sets of 4-substituted pyridopyrrolopyrimidine nucleobases were prepared through nucleophilic substitutions or cross-coupling reactions of 4-chloropyridopyrrolopyrimidines. The corresponding 4-amino-pyridopyrrolopyrimidines were glycosylated with 5--tritylribose using the modified Mitsunobu protocol. Several examples of the title heterocycles showed blue or green fluorescence.
View Article and Find Full Text PDFMol Divers
November 2021
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.
An efficient, eco-friendly protocol has been described for the chemoselective synthesis of tetracyclic pyrido-fused dibenzodiazepines derivatives via catalyst-free, three-component reaction of dimedone, 1,2-diamines, 3-formylchromones, and malononitrile. The significant advantages of this cascade approach are to create two new rings and four new σ bonds containing three C-N and one C-C bond, as well as the breakdown of a C-O bond.
View Article and Find Full Text PDFChemistry
October 2020
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.
All four isomeric series of novel 4-substituted pyrido-fused 7-deazapurine ribonucleosides possessing the pyridine nitrogen atom at different positions were designed and synthesized. The total synthesis of each isomeric fused heterocycle through multistep heterocyclization was followed by glycosylation and derivatization at position 4 by cross-coupling reactions or nucleophilic substitutions. All compounds were tested for cytostatic and antiviral activity.
View Article and Find Full Text PDFRSC Adv
May 2018
Faculty of Chemical Engineering, HCMC University of Technology, VNU-HCM 268 Ly Thuong Kiet Street, District 10 Ho Chi Minh City Vietnam +84 8 38637504 +84 8 38647256 ext. 5681.
A new pathway to access pyrido-fused quinazolinones a Cu(OAc)-catalyzed domino sequential transformation between 2'-haloacetophenones and 2-aminopyridines was demonstrated. The solvent and base exhibited a remarkable effect on the transformation, in which the combination of DMSO and NaOAc emerged as the best system. Cu(OAc)·HO was more active towards the reaction than numerous other catalysts.
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