Topic
Annulation
About: Annulation is a research topic. Over the lifetime, 10152 publications have been published within this topic receiving 189701 citations.
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TL;DR: The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same α-oxoketene-N,S-arylaminoacetal under the similar reaction conditions making this new strategy highly useful in diversity oriented synthesis (DOS).
57 citations
TL;DR: The radical C(sp2)-H sulfonylation and C( sp2)-N bond oxygenation enabling the chemo-selective synthesis of 3-sulfonyl chromones using enaminones and sulfonyl hydrazines have been accomplished.
57 citations
TL;DR: In this article, a dipeptide phosphine catalyst with an l-d configuration was employed to obtain α-selective [3 + 2] annulation products with good regioselectivities and enantioselectivity.
Abstract: Catalyst-controlled regiodivergent [3 + 2] annulations of aurones and allenoates have been developed. When a dipeptide phosphine catalyst with an l-d- configuration was employed, α-selective [3 + 2] annulation products could be obtained with good regioselectivities and enantioselectivities. With the employment of l-l- dipeptide phosphines, γ-selective annulation products could be selectively obtained with excellent enantioselectivities. By simply tuning the catalyst configurations, a wide range of α-selective or γ-selective spirocyclic benzofuranones with either aryl or alkyl substitutions could be readily prepared. DFT calculations suggest that the conformation of the dipeptide phosphines influences the hydrogen bonding interactions or the distortion energy, resulting in delicate energy differentiation in the transition states, and accounting for the observed regioselectivity.
57 citations
TL;DR: A proposed mechanism for the synthesis of 1,3-benzoxazine derivatives involves the formation of the expected 2-amino-3-(1-hydroxyalkyl)naphthalenes, followed by their condensation with an iminium ion species formed from the trialkylamine base used in the reaction.
Abstract: Intramolecular carbopalladation of the cyano group has been employed for the synthesis of 3,4-disubstituted 2-aminonaphthalenes. (2-Iodophenyl)acetonitrile reacts with a variety of internal alkynes to afford 2-aminonaphthalenes in high yields with good regioselectivity. The scope and limitations of this process, which proceeds by the intramolecular addition of a vinylpalladium species to the triple bond of the cyano group, have been studied. The annulation of certain hindered propargylic alcohols affords 1,3-benzoxazine derivatives, rather than the expected 2-aminonaphthalenes. The involvement of trialkylamine bases in the formation of these heterocyclic compounds has been established. A proposed mechanism for the synthesis of 1,3-benzoxazine derivatives involves the formation of the expected 2-amino-3-(1-hydroxyalkyl)naphthalenes, followed by their condensation with an iminium ion species formed from the trialkylamine base used in the reaction.
57 citations
TL;DR: A nickel/NHC system for regioselective oxidative annulation by double C-H bond activation and concomitant alkyne insertion is described, which plays a double role as a two-component coupling partner and as a hydrogen acceptor.
Abstract: A nickel/NHC system for regioselective oxidative annulation by double C-H bond activation and concomitant alkyne insertion is described. The catalytic reaction requires a bidentate directing group, such as an 8-aminoquinoline, embedded in the substrate. Various 5,6,7,8-tetrasubstituted-N-(quinolin-8-yl)-1-naphthamides can be prepared as well as phenanthrene and benzo[h]quinoline amide derivatives. Diarylalkynes, dialkylalkynes, and arylalkylalkynes can be used in the system. A Ni(0)/Ni(II) catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two-component coupling partner and as a hydrogen acceptor.
57 citations