Full length articleReactions of THEBAINE (cas 115-37-7) derivatives with trifluoroacetyl acetylenes: [4+2]-addition solely

Add time:08/25/2019    Source:sciencedirect.com

Trifluoroacetyl acetylenes, highly reactive dienophiles and electrophiles, were used as the probe for study competitive [4+2] vs nucleophilic addition reactions in THEBAINE (cas 115-37-7) series. Unlike thebaine itself that reacts with these electron deficient acetylenes giving rise to the adducts resulted from the nucleophilic attack of the nitrogen at the alkyne carbon, the reactions of N-acyl-N-northebaines with trifluoroacetyl acetylenes furnished the [4+2]-adducts solely. The last ones readily rearranged to the corresponding 3H-furo[4,3,2-fg][3]benzazocine derivatives. So, the use of N-acyl-N-northebaines as the starting materials in the reactions with acetylenic dienophiles provides the general methodology to avoid a formation of the undesirable “nucleophilic” adducts typical for the reactions of the natural alkaloid thebaine.

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