571184-11-7Relevant articles and documents
Synthesis of Fused Pyrimido[1,6- a ]indolones via Rhodium(III)-Catalyzed Cascade Annulations
Raji Reddy, Chada,Bodasu, Srinivas,Mallesh, Kathe,Prapurna, Y. Lakshmi
, p. 1127 - 1136 (2020/10/29)
A novel method for the synthesis of fused pyrimido[1,6- a ]-indolone derivatives by annulation of 2-alkynylaryl aldehydes/2-alkynyl arylidene ketones with N -(pivaloyloxy)-1 H -indole-1-carboxamide catalyzed by rhodium has been accomplished. The reaction proceeds through C-H activation based annulation with alkyne moiety followed by addition of nitrogen on to aldehyde/activated alkene to give the products in moderate to good yields. Highly fluorescent dipyrrinone analogues could be synthesized from the derived products.
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.
Silver-Catalysed Domino Approach to 1,3-Dicarbo-Substituted Isochromenes
Dell'Acqua, Monica,Pirovano, Valentina,Peroni, Stefano,Tseberlidis, Giorgio,Nava, Donatella,Rossi, Elisabetta,Abbiati, Giorgio
supporting information, p. 1425 - 1433 (2017/04/01)
We report herein the first example of the silver triflate catalysed synthesis of 1,3-dicarbo-substituted isochromene derivatives starting from 2-alkynyl(hetero)arylaldehydes and enolizable ketones. The reaction proceeds in a cascade fashion under mild heating with complete regioselectivity and moderate-to-good yields. In some cases, the reaction gives unexpected homodimeric products. Two competitive mechanistic paths for the formation of the desired isochromene derivatives and the homodimeric products are described.
