1394123-41-1Relevant articles and documents
Iodine-mediated synthesis of benzo[: A] fluorenones from yne-enones
Akbar, Sikkandarkani,John Tamilarasan,Srinivasan, Kannupal
, p. 23652 - 23657 (2019)
The chalcones derived from o-alkynylacetophenones and aromatic aldehydes (yne-enones) when heated under reflux with iodine in acetic acid gave a range of benzo[a]fluorenone derivatives in moderate to good yields. The transformation involves the formation of a vinyl indenone intermediate through regioselective alkyne hydration and intramolecular aldol condensation followed by electrocyclic ring closure and aromatization.
Radical-Triggered Tandem Cyclization of 1,6-Enynes with H2O: A Way to Access Strained 1 H-Cyclopropa[ b]naph thalene-2,7-diones
Zheng, Limeng,Zhou, Bingwei,Jin, Hongwei,Li, Ting,Liu, Yunkui
supporting information, p. 7053 - 7056 (2018/11/24)
A radical-triggered tandem cyclization of 1,6-enynes has been developed herein. Strained 1H-cyclopropa[b]naphthalene-2,7-diones are successfully obtained in moderate to good yields with excellent stereoselectivity. Mechanistic studies reveal a key role of water in generating a hydroxyl radical that initiates a sequential Michael addition/ring closure pathway. Importantly, the formed hydroxyl is proposed to be a good leaving group during the cyclopropane ring formation.