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Synthesis of the Benzo[b]fluorene Core of the Kinamycins by Arylalkyne–Allene and Arylalkyne–Alkyne Cycloadditions

✍ Scribed by Esther González-Cantalapiedra; Óscar de Frutos; Carmen Atienza; Cristina Mateo; Antonio M. Echavarren


Book ID
102175879
Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
257 KB
Volume
2006
Category
Article
ISSN
1434-193X

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Non-conjugated benzotriynes 2 undergo a novel radical cycloaromatization to provide the benzo[b]fluorene core of the kinamycins. The overall process involves a thermal intramolecular cyclization to the non-benzenoid biradicals 4 followed by radical cyclization and hydrogen abstraction.

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## Abstract A convenient and general approach to the synthesis of 2‐substituted 3‐bromobenzofurans and ‐benzothiophenes was developed. The procedure is based on the cyclization of __ortho__‐substituted arylalkynes in the presence of __N__‐methylpyrrolidin‐2‐one hydrotribromide (MPHT) as a soft and