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Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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97 citations
TL;DR: In this paper, a solid-phase assembly of model peptides derived from human parathyroid hormone-related protein (11−19) containing ω-azido- and ωyl-α-amino acid residues in positions i and i+4 was cyclised in solution by an intramolecular CuI-catalyzed azide-alkyne 1,3-dipolar Huisgen cycloaddition.
97 citations
TL;DR: Trifluoromethyl substituted quinolines have been prepared by 1, 2- or 1, 4- addition of anilines to trifluoroacetyl acetylenes followed by intramolecular acid catalyzed ring closure.
97 citations
TL;DR: A novel multicomponent reaction of arynes, beta-keto sulfones, and Michael-type acceptors is presented, providing an efficient method for the synthesis of polysubstituted naphthols and polysubstantial naphthalenes.
Abstract: A novel multicomponent reaction of arynes, beta-keto sulfones, and Michael-type acceptors is presented, providing an efficient method for the synthesis of polysubstituted naphthols and polysubstituted naphthalenes. Further investigation suggests that the tandem reaction may proceed via a sequential nucleophilic attack to arynes, intramolecular nucleophilic substitution followed by a Michael addition, and a ring closure-elimination process.
96 citations
TL;DR: While microwave irradiation was found to be determinant on the reaction efficiency, the choice of ligand diverged the reaction pathways and intramolecular alpha-CH arylation of tertiary amide occurred to furnish the oxindoles.
Abstract: Linear amides 4, prepared in one step by the Ugi four-component reaction, were converted to 3,4-dihydroquinoxalin-3-ones (5) or to 2-(2-oxoindolin-1-yl)acetamides (6) dependent on the catalytic conditions. While microwave irradiation was found to be determinant on the reaction efficiency, the choice of ligand diverged the reaction pathways. Heating a solution of 4 in dioxane/MeCN (v/v = 85/15) under microwave irradiation conditions in the presence of Pd(dba)2 (0.05 equiv) and Cs2CO3 (2 equiv), using XPhos as a supporting ligand, afforded the 3,4-dihydroquinoxalin-3-ones (5) via an intramolecular N-arylation of the secondary amide. On the other hand, using BINAP as ligand under otherwise identical conditions, intramolecular α-CH arylation of tertiary amide occurred to furnish the oxindoles (6).
96 citations