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Gold(I)‐Catalyzed 6‐ endo ‐Dig Hydrative Cyclization of an Alkyne‐Tethered Ynamide: Access to 1,6‐Dihydropyridin‐2(3 H )ones
Author(s) -
Ghosh Nayan,
Nayak Sanatan,
Sahoo Akhila K.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301599
Subject(s) - alkyne , dig , chemistry , catalysis , isomerization , combinatorial chemistry , conjugate , computer science , organic chemistry , world wide web , mathematics , mathematical analysis
Hydrate your chemistry! Hydrative cyclization of 5‐yne‐ynamides in the presence of Echavarren's catalyst and p ‐toluenesulphonic acid (PTSA) ⋅ H 2 O at room temperature affords an array of 1,6‐dihydropyridin‐2(3 H )one derivatives. Isomerization, epoxidation, and hydrogenation of the double bond and insertion of an extended π‐conjugate system into the pyridinone skeleton have been successfully accomplished (see scheme; Ts=tosyl).