18450-27-6Relevant articles and documents
Synthesis and transformations of ethyl 3-formyl-1H-indole-2-carboxylate. Preparation of aplysinopsin and β-carboline thiohydantoin analogues
Jak?e, Renata,Bevk, David,Golobi?, Amalija,Svete, Jurij,Stanovnik, Branko
, p. 413 - 419 (2006)
Various aplysinopsin and β-carboline thiohydantoin analogues were prepared starting from ethyl 3-formyl-1H-indole-2-carboxylate by condensation with the active methylene group of 2-thiohydantoin, rhodanine, or thiobarbituric acid derivatives.
KOH-mediated stereoselective alkylation of 3-bromooxindoles for the synthesis of 3,3′-disubstituted oxindoles with two contiguous all carbon quaternary centres
Devi, Manju,Jadhav, Amol P.,Singh, Ravi P.
supporting information, p. 8445 - 8448 (2021/05/25)
The stereoselective synthesis of 3,3′-disubstituted oxindoles having all-carbon quaternary stereocenters has been achieved using KOH as a base with an excellent diastereomeric ratio (98?:?2). The practicability of the present methodology has been validated with the synthesis of a series of substrates in good to excellent yields. The aesthetic simplicity, accessibility, and eco-friendly base (KOH) have prompted the broader application of the present methodology in organic synthesis.
A highly selective ratiometric fluorescent probe for H2S based on new heterocyclic ring formation and detection in live cells
Samanta, Sandip Kumar,Ali, Syed Samim,Gangopadhyay, Ankita,Maiti, Kalipada,Pramanik, Ajoy Kumar,Guria, Uday Narayan,Ghosh, Aritri,Datta, Pallab,Mahapatra, Ajit Kumar
, p. 349 - 360 (2019/03/26)
A 3-indolylacrylate derivative, 3-IA, prepared by connecting an ethyl acrylate in 3-position of indole has been synthesised and characterised. Ethyl acrylate moiety acts as the Michael acceptor towards H2S, and the resultant addition product then participates in intramolecular cyclisation with the ester group at 2-position to form another new heterocyclic ring. Blue fluorescence of 3-IA turned into green in presence of H2S, leading to ratiometric behaviour of the fluorescent sensor with large stokes shift of 55 nm. Probe 3-IA has excellent selectivity towards H2S over other biothiols and other competing anions. Density function theory/time-dependent density function theory calculations were carried out to validate the reaction mechanism and the electronic properties of 3-IA. Importantly, the ratiometric probe 3-IA shows great promise in H2S detection by simple visual fluorescent inspection in filter paper-based protocol. The probe shows its excellent ability to detect H2S in different natural water samples. Furthermore, we have employed our probe to detect H2S for ratiometric imaging in live Vero cell.
Acetic anhydride to the rescue: Facile access to privileged 1,2,3,4-tetrahydropyrazino[1,2-a]indole core via the Castagnoli-Cushman reaction
Chizhova, Maria,Khoroshilova, Olesya,Dar'in, Dmitry,Krasavin, Mikhail
supporting information, p. 3612 - 3615 (2018/09/11)
Indole-fused cyclic anhydrides earlier deemed unreactive in the Castagnoli-Cushman reaction with imines have been rendered valid participant in this process. The new reaction format involves the use of respective indole-based dicarboxylic acids and in sit