One-pot synthesis of janusene N-methyl-5a,11a-dicarboximide employing 2,3-dibromo-N-methylmaleimide as acetylene equivalent

Davor Margetic; Petar Strbac

doi:10.3390/ecsoc-24-08426

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One-pot synthesis of janusene N-methyl-5a,11a-dicarboximide employing 2,3-dibromo-N-methylmaleimide as acetylene equivalent

Davor Margetic

^*,

Petar Strbac

¹ Laboratory for Physical-Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, 10001 Zagreb, Croatia

Published: 14 November 2020 by MDPI in The 24th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-24-08426

Abstract:

Synthesis of janusene (5,5a,6,11,11a,12-hexahydro-5,12:6,11-di-o-benzenonaphthacene) requires several reaction steps starting from anthracene. In this account, one-pot, three steps synthesis of janusene N-methyl-5a,11a-dicarboximide employing 2,3-dibromo-N-methylmaleimide as acetylene equivalent is described. This thermal reaction is simple synthetic procedure in comparison to sequential-multi step [4+2] cycloaddition routes. Here 2,3-dibromo-N-methylmaleimide acts effectively as ' molecular glue ' bridging two anthracene molecules.

Keywords: organic synthesis; cycloaddition reaction; Diels-Alder reaction

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Davor Margetic

Petar Strbac