Traceless synthetic approach towards oxaza-dicyclopenta[a,h]naphthalenes under solvent-free condition: a basic alumina-supported green protocol

Paira, Rupankar; Mondal, Shyamal; Chowdhury, Arpan; Banerjee, Minakshi; Maity, Arindam; Hazra, Abhijit; Mondal, Nirup B.

doi:10.1016/j.tetlet.2013.03.095

Cited by 5 publications

(1 citation statement)

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“…On the other hand, sequential/consecutive reactions are considered to be stepwise reactions with relatively stable, yet reactive, intermediates, where the individual steps can be performed separately. External reagents or changes in reaction conditions are required in such reactions to facilitate the tandem process, enabling multicomponent tandem reactions (MCTRs).…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Tandem Reactions and Polymerizations of Alkynes, Carbonyl Chlorides, and Thiols

et al. 2015

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Multicomponent tandem reactions (MCTRs), with multiple bonds formed in a highly concise fashion in a single vessel, have been noted as one of the most powerful and popular synthetic strategies in modern organic chemistry. Attracted by their operational simplicity, synthetic efficiency, high atom economy, and environmental benefit, the MCTRs and the corresponding multicomponent tandem polymerizations (MCTPs) of alkynes, carbonyl chlorides, and aliphatic/aromatic thiols were developed. By combining the Sonogashira coupling reaction between alkynes and carbonyl chlorides, and the hydrothiolation reaction of electron-deficient alkynone intermediates, high atom economy was achieved in such one-pot, two-step, three-component reactions/polymerizations. The MCTPs can proceed efficiently under mild conditions near room temperature to afford sulfur-rich polymers with high molecular weight, high yield, high regioselectivity, and good stereoselectivity. Through the MCTPs of different combination of monofunctional and bifunctional monomers, polymers with tunable backbone structures and photophysical properties can be obtained. These polymers generally possess good solubility and film-forming ability. Their thin films enjoy high refractivity, and their photosensitivity enables easy modulation of the thin film refractive indices.

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Section: Introductionmentioning

confidence: 99%

Multicomponent Tandem Reactions and Polymerizations of Alkynes, Carbonyl Chlorides, and Thiols

et al. 2015

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ChemInform Abstract: Traceless Synthetic Approach Towards Oxaza‐dicyclopenta[a,h]naphthalenes under Solvent‐Free Condition: A Basic Alumina Supported Green Protocol.

et al. 2013

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Synthesis of 6a,6b,13,13a-tetrahydro-6H-5-oxa-12a-azadibenzo[a,g]fluorene derivatives via cycloaddition reactions of isoquinolinium salts with 3-nitrochromenes

Fang

Yan

2013

Mol Divers

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An efficient and diastereoselective synthetic procedure for functionalized 6a,6b,13,13a-tetrahydro-6H-5-oxa-12a-azadibenzo[a,g]fluorene derivatives was successfully developed by the cycloaddition reaction of isoquinolinium salts and 3-nitrochromenes with triethylamine as base in ethanol at room temperature. 1H NMR data and single crystal structures confirm the production and isolation of a single stereoisomer.

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Traceless synthetic approach towards oxaza-dicyclopenta[a,h]naphthalenes under solvent-free condition: a basic alumina-supported green protocol

Cited by 5 publications

References 41 publications

Multicomponent Tandem Reactions and Polymerizations of Alkynes, Carbonyl Chlorides, and Thiols

Multicomponent Tandem Reactions and Polymerizations of Alkynes, Carbonyl Chlorides, and Thiols

ChemInform Abstract: Traceless Synthetic Approach Towards Oxaza‐dicyclopenta[a,h]naphthalenes under Solvent‐Free Condition: A Basic Alumina Supported Green Protocol.

Synthesis of 6a,6b,13,13a-tetrahydro-6H-5-oxa-12a-azadibenzo[a,g]fluorene derivatives via cycloaddition reactions of isoquinolinium salts with 3-nitrochromenes

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