Concise Synthesis of Chromene/Chromane-Type Aryne Precursors and Their Applications.
J Org Chem
; 86(9): 6765-6779, 2021 05 07.
Article
in En
| MEDLINE
| ID: mdl-33852309
ABSTRACT
The gram-scale synthesis of 5,6-, 6,7-, and 7,8-chromene/chromane-type aryne precursors and their applications in regioselective transformation to other functional derivatives is reported. Chromene/chromane-type arynes are generated under mild conditions, which can further undergo [2 + 2], [3 + 2], and [4 + 2] cycloaddition reactions, nucleophilic addition reactions, and σ-insertion reactions to produce structurally novel substituted chromenes and chromanes. The excellent regioselectivity of the reaction is facilitated by the oxygen-containing guiding groups at the ortho-position of the triple bond, which can be removed or switched to other functional groups including alkenyl, aryl, heteroaryl, and arylamino groups.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Benzopyrans
Language:
En
Journal:
J Org Chem
Year:
2021
Document type:
Article