The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations

Nagam Satish; Siruvuri Krishnam Raju; Jagadeesh Babu Nanubolu; Gangarajula Sudhakar

doi:10.1039/D1NJ03654H

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The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations†

Nagam Satish,^ab Siruvuri Krishnam Raju,^ab Jagadeesh Babu Nanubolu^c and Gangarajula Sudhakar

*^ab

Author affiliations

* Corresponding authors

^a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, Telangana, India
E-mail: gsudhakar@iict.res.in

^b Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, UP, India

^c Department of Analytical & Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, Telangana, India

Abstract

The reaction of aryl vinyl epoxides and carbonyl compounds in the presence of a catalytic amount of BF₃·OEt₂ to indeno[de]isochromenes via tandem Nazarov and oxa-Pictet–Spengler cyclizations is described. The protocol used was operationally simple and the synthesis generated three bonds (two C–C and one C–O), thereby providing a structural skeleton of pharmaceutical interest and natural-product-like polycyclic frameworks.

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DOI: https://doi.org/10.1039/D1NJ03654H
Article type: Paper
Submitted: 29 Jul 2021
Accepted: 04 Aug 2021
First published: 17 Aug 2021

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New J. Chem., 2021,45, 16248-16253

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The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations

N. Satish, S. K. Raju, J. B. Nanubolu and G. Sudhakar, New J. Chem., 2021, 45, 16248 DOI: 10.1039/D1NJ03654H

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New Journal of Chemistry

The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations†

Abstract

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The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations

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