73825-35-1Relevant articles and documents
A four-component domino reaction: An eco-compatible and highly efficient construction of 1,8-naphthyridine derivatives, their in silico molecular docking, drug likeness, ADME, and toxicity studies
Garg, Ankita,Tadesse, Aschalew,Eswaramoorthy, Rajalakshmanan
, (2021/04/26)
A multicomponent domino reaction of enaminone, malononitrile, and o-phthalaldehyde has been established, providing direct access to novel highly functionalized pentacyclic cyclopenta [b] indeno [1, 2, 3-de] [1,8] naphthyridine derivatives. The simplicity of execution, readily available substrates, high yields, excellent functional group tolerance, scalability, and good scores of environmental parameters make this synthetic strategy more sustainable and worthy of further attention. This one-pot transformation, which involved multiple steps and did not require the use of a catalyst, constructed four new C-C bonds, two new C-N bonds, and three new rings, with efficient use of all reactants. Furthermore, we performed in silico molecular docking analysis for prediction of anticancer (against human topoisomerase IIβ protein) and antimicrobial (against E.coli. DNA gyrase B protein) activities. Drug likeness and ADMET studies were also predicted. Overall investigation indicates that compound 6i may serve as a candidate that could be developed as potential anticancer and antimicrobial agent among all.
Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis
Bhattacherjee, Dhananjay,Ram, Shankar,Chauhan, Arvind Singh,Yamini,Sheetal,Das, Pralay
supporting information, p. 5934 - 5939 (2019/04/08)
A highly efficient and flexible protocol for intramolecular annulation of exocyclic β-enaminones has been disclosed for the synthesis of carbazolones and imidazo[1,2-a]pyridines through a counter-anion-controlled free-radical mechanism promoted by hypervalent iodine(III). The cooperative behavior of HTIB and AgSbF6 plays a crucial role in the intramolecular annulation process through C?C and C?N bond formation to give the desired products. The mechanistic insights suggest that the two competitive reactions involved in the system are guided by the nature of the counteranion, which determines the formation of the final products. A wide variety of carbazolones and imidazo[1,2-a]pyridine molecules have been prepared and isolated in good to excellent yields.
Synthesis of N-substituted carbazolones from α-iodo enaminones via Pd(0)-catalyzed intramolecular coupling under microwave irradiation
Yun, Xi-Liu,Bi, Wen-Ying,Huang, Jian-Hui,Liu, Yu,Zhang-Negrerie, Daisy,Du, Yun-Fei,Zhao, Kang
supporting information; experimental part, p. 5076 - 5080 (2012/09/25)
A variety of N-aryl and N-alkyl carbazolones were conveniently achieved in good to high yields via Pd2(dba)3-mediated intramolecular coupling of N-substituted α-iodo enaminones under microwave irradiation. The Pd(0)-catalyzed cyclization was found to proceed favorably with the more electron-deficient phenyl ring during the reactions involving unsymmetrical N,N-diaryl α-iodo enaminones. This unique property enables the construction of carbazolone skeleton containing nitro substituted benzenoid ring.
