An efficient synthesis of substituted chrysenes

Abstract

Substituted chrysenes have been swiftly synthesised by the 6-endo-dig cyclisation of ethynylnaphthalenes using platinum(II) chloride. Cyclisation precursors were directly prepared from commercially available 2-bromoaldehydes in a telescoped synthetic procedure involving a Cannizzaro triggered cascade and subsequent dehydration and desilylation. This short synthetic procedure allows rapid access to derivatives of biologically active molecules with useful electronic properties.

Nanographene and Graphene Nanoribbon Synthesis via Alkyne Benzannulations

“…Chrysene 69 can be further functionalized though bromination at the 3-, 6-, 9-, 12-postions to afford tetrabrominated chrysene which can undergo Pd-catalyzed crosscoupling to afford chrysene derivatives 70 [83,87]. An analogous version of this reaction has also been reported using microwave irradiation to arrive at other substitution patterns of chrysene [88].…”

Novel Approach Towards the Synthesis of Poly Heterocyclic Compounds: Total Synthesis of 12-Oxa-6,10b-epoxy-4b,5,6,10b,11,12-hexahydrochrysene

“…Substituted hexahydro-chrysenes are known to show biological activity and estrogenic potency [13]. Literature reports the synthesis of substituted chrysenes [14] and hexahydrochrysenes [15,16]. In these syntheses, various routes have been adopted to produce func-tional groups in a highly stereoselective manner.…”