Issue 69, 2014

A facile access to substituted benzo[a]fluorenes from o-alkynylbenzaldehydes via in situ formed acetals

Abstract

In situ formed acetal changes the course of Brønsted acid-catalyzed reaction of ortho-alkynylbenzaldehydes with arylalkynes altogether. By utilizing this, an efficient domino approach for the regioselective synthesis of substituted benzo[a]fluorenes has been developed under mild reaction conditions. In situ formed acetal facilitates the intermolecular heteroalkyne metathesis and subsequent trans to cis isomerization of a double bond to effect the intramolecular annulation.

Graphical abstract: A facile access to substituted benzo[a]fluorenes from o-alkynylbenzaldehydes via in situ formed acetals

Supplementary files

Article information

Article type
Communication
Submitted
22 May 2014
Accepted
01 Jul 2014
First published
08 Jul 2014

Chem. Commun., 2014,50, 9925-9928

Author version available

A facile access to substituted benzo[a]fluorenes from o-alkynylbenzaldehydes via in situ formed acetals

S. Manojveer and R. Balamurugan, Chem. Commun., 2014, 50, 9925 DOI: 10.1039/C4CC03934C

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