We report the discovery of an anomalous reaction of 2-(alkynonyl)alkynylbenzenes under AgI catalysis for the selective formation of isocoumarins. This reaction is previously undocumented for 2-(alkynonyl)alkynylbenzenes in terms of the reaction mechanism and the product formed. Water (H2O18) labeling studies suggested a possible mechanistic pathway in which the initial formation of a pyrylium ion is followed by hydrative dealkynylation, that is, water incorporation and alkyne expulsion, similar to a retro-Favorskii reaction. © 2019 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim

Beeraiah Baire

Department Of Chemistry

Jampani Santhi

chemistry

Hydration

Synthesis (chemical)

Alkynes

DEALKYNYLATION

ISOCOUMARINS

ISOTOPIC LABELING

Mechanistic pathways

Natural products

reaction mechanism

Selective formation

Hydrocarbons

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Chemistry - An Asian Journal

A new strategy for the synthesis of 3-arylisocoumarins and 8-hydroxy-3-arylisocoumarins was investigated by using acyl anion chemistry for the initial C-C bond formation. The obtained keto esters and keto lactones as intermediates underwent based-promoted intramolecular cyclization to afford 3-arylisocoumarins in good yields. The developed methodology was applied for the synthesis of the important natural products thunberginol A and cajanolactone A. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

European Journal of Organic Chemistry

Synthesis of 3-arylisocoumarins by using acyl anion chemistry and synthesis of thunberginol A and cajanolactone A

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

Cambridge Crystallographic Data Centre (CCDC)

Angewandte Chemie International Edition

Ruthenium(II)-Catalyzed CH Activation/Alkyne Annulation by Weak Coordination with O2as the Sole Oxidant

Spotlights on our sister journals: Eur. J. Org. Chem. 21/2012

The Journal of Organic Chemistry

Silver(I)-Catalyzed Novel Cascade Cyclization Reactions: Incorporation of Allenes into the Isochromenes

An Unusual Conversion of 2-(Alkynonyl)Alkynylbenzenes to Isocoumarins by a Retro-Favorskii-like Degradation

Journal	Data powered by TypesetChemistry - An Asian Journal
Publisher	Data powered by TypesetJohn Wiley and Sons Ltd
ISSN	18614728
Open Access	No