BF3·OEt2-catalyzed synthesis of 2,2′-spirobi-2H-1-benzopyrans from 2H-chromenes

Sairam Mudulkar; Sai Teja Kolla; Balasubramanian Sridhar; China Raju Bhimapaka

doi:10.1039/D2OB01286C

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BF₃·OEt₂-catalyzed synthesis of 2,2′-spirobi-2H-1-benzopyrans from 2H-chromenes†

Sairam Mudulkar,^a Sai Teja Kolla,

^a Balasubramanian Sridhar

^b and China Raju Bhimapaka

*^a

Author affiliations

* Corresponding authors

^a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India
E-mail: chinaraju@iict.res.in

^b Department of Analytical & Structural Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India

Abstract

A new BF₃·OEt₂-catalyzed approach was developed for the construction of 2,2′-spirobi-2H-1-benzopyrancarboxylates by reacting ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-3-carboxylates with salicylaldehydes. The reactions proceeded through the formation of C–C and C–O bonds in one pot. Structure assignment of compound 3c was confirmed by single crystal X-ray analysis.

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Article information

DOI: https://doi.org/10.1039/D2OB01286C
Article type: Paper
Submitted: 18 Jul 2022
Accepted: 04 Oct 2022
First published: 08 Oct 2022

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Org. Biomol. Chem., 2022,20, 8145-8148

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BF₃·OEt₂-catalyzed synthesis of 2,2′-spirobi-2H-1-benzopyrans from 2H-chromenes

S. Mudulkar, S. T. Kolla, B. Sridhar and C. R. Bhimapaka, Org. Biomol. Chem., 2022, 20, 8145 DOI: 10.1039/D2OB01286C

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Organic & Biomolecular Chemistry