We have developed a metal-free, N-iodosuccinimide (NIS)-promoted, cascade strategy for the efficient synthesis of biologically important indeno[1,2-c]pyrroles via a [3+2] annulation process of enamine-alkynes. This methodology had shown a very broad scope for diversely functionalized enamines and alkynes. We have also developed a one-pot, multicomponent strategy for the direct synthesis of indeno-pyrroles from diynones via enamine-alkynes. Control experiments supported the involvement of NIS as an electrophilic activator via an ionic mechanism rather than a radical pathway. (Figure presented.). © 2016 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim

Beeraiah Baire

Department Of Chemistry

Jampani Santhi

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

Advanced Synthesis and Catalysis

In the present work, a novel donor (D)-acceptor (A) fluorophore based on indeno-pyrrole derivative (PYROMe) has been utilized as a dual sensor for volatile acids and aromatic amines, where sensory responses were regulated by the aggregation-induced emission (AIE) property. The twisted structural framework of PYROMe, confirmed by crystal study, avoids closed cofacial encounter upon aggregation and aided with augmented rigidity via different noncovalent interactions that ultimately ensued restricted intramolecular rotation (RIR). Consequently, PYROMe exhibited AIE in THF/H2O mixture along with bright solid-state emission. The accessibility of protonation at carbonyl site and feasible HOMO energy to accept electrons from aromatic amines during photoexcitation enabled PYROMe as a potential dual sensor. A thin film of PYROMe was utilized for the quantitative detection of volatile acids and aromatic amines, and the detection limit (DL) was found to be as low as 0.77 ppm and 6.04 ppb for trifluoroacetic acid (TFA) and aniline vapors, respectively. Beyond the established scopes of substituted indeno-pyrroles, the present study paves the way, for the first time, toward an AIE-driven dual-stimuli response in indeno-pyrrole based D-A fluorophores. © 2019 American Chemical Society.

ACS Applied Materials and Interfaces

Aggregation-Induced Emission Active Donor-Acceptor Fluorophore as a Dual Sensor for Volatile Acids and Aromatic Amines

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

Cambridge Crystallographic Data Centre (CCDC)

Fuel

A reaction mechanism for tar decomposition at moderate temperatures with any coal type

Organic Letters

Generation of Indeno[1,2-c]pyrroles via a Pd-Catalyzed Reaction of 2-Alkynylbromobenzene with Propargylic Sulfonamide

Chemistry - A European Journal

Palladium-Catalyzed Synthesis of 7,9-Diaryl-8 H-acenaphtho[1,2-c]pyrroles and Their Application in Explosives Detection

Four Iodine-Mediated Electrophilic Cyclizations of Rigid Parallel Triple Bonds Mapped from 1,8-Dialkynylnaphthalenes

N-Iodosuccinimide-Promoted Rapid Access to Indeno[1,2-c]pyrroles via [3+2] Annulation of Enamine-alkynes

Journal	Data powered by TypesetAdvanced Synthesis and Catalysis
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	16154150
Open Access	No