129461-23-0Relevant articles and documents
Synthesis of 5-chloropyrrole carboxaldehydes from 5-oxopyrrolidine carboxamides
Netchitailo, Pierre,Othman, Mohamed,Daich, Adam,Decroix, Bernard
, p. 3227 - 3230 (1997)
N-alkyl-5-chloropyrrole-2(or 3)-carboxaldehydes are obtained by treatment of N-alkyl-5-oxopyrrolidine-2 (or 3)-carboxamides by phosphorus oxychloride and basic hydrolysis.
Metal free coupling of heteroaryl N-tosylhydrazones and thiols: Efficient synthesis of sulfides
García-Carrillo, Mario Alfredo,Guzmán, ángel,Díaz, Eduardo
supporting information, p. 1952 - 1956 (2017/04/27)
A metal free coupling of heteroaromatic N-tosylhydrazones with thiols is presented. A convenient synthetic route to synthesize heteroaryl N-tosylhydrazones is also showed. Valuable thioethers with pyrroles, pyridines, thieno[2,3-b]pyridines, imidazo[1,2-a]pyridines, and 6H-thieno[2,3-b]pyrroles derivatives were synthesized in good yields. This coupling reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using heteroaryl aldehydes, without the need to isolate the N-tosylhydrazone.
Modulating reactivity and diverting selectivity in palladium-catalyzed heteroaromatic direct arylation through the use of a chloride activating/blocking group
Liegault, Benoit,Petrov, Ivan,Gorelsky, Serge I.,Fagnou, Keith
supporting information; experimental part, p. 1047 - 1060 (2010/04/04)
(Chemical Equation Presented) Through the introduction of an aryl chloride substituent, the selectivity of palladium-catalyzed direct arylation may be diverted to provide alternative regioisomeric products in high yields. In cases where low reactivity is typically observed, the presence of the carbon-chlorine bond can serve to enhance reactivity and provide superior outcomes. From a strategic perspective, the C-Cl bond is easily introduced and can be employed in a variety of subsequent transformations to provide a wealth of highly functionalized heterocycles with minimal substrate preactivation. The impact of the C-Cl functional group on direct arylation reactivity has also been evaluated mechanistically, and the observed reactivity profiles correlate very well with that predicted by a concerted metalation-deprotonation pathway.
Vilsmeier-Haack reaction with succinamidals. A convenient synthesis of 5-chloropyrrole-2-carboxaldehydes and 5-chloropyrrole-2,4-dicarboxaldehydes
Guzman, Angel,Romero, Moises,Muchowski, Joseph M.
, p. 791 - 794 (2007/10/02)
It is shown that the reaction of N-alkylsuccinamidals (2) with Vilsmeier-Haack reagent derived from DMF and phosphorus oxychloride can be controlled to preferentially produce either 5-chloropyrrole-2-carboxaldehydes (8) or 5-chloropyrrole-2,4-dicarboxalde