21402-85-7Relevant articles and documents
An unusual approach to spirolactones and related structures
Guindeuil, Soizic,Zard, Samir Z.
, p. 665 - 667 (2006)
Spirocyclic structures can be obtained by an ipso-type radical cyclisation onto a furan or a suitably substituted pyrrole followed by oxidation of the stabilised radical adduct. The Royal Society of Chemistry 2006.
-
Hiraoka
, p. 2955 (1973)
-
Dealkoxylation ofN-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis
Suzuki, Hirotsugu,Shiomi, Takahiro,Yoneoka, Kenji,Matsuda, Takanori
supporting information, p. 7545 - 7548 (2020/10/15)
Lewis acid-assisted palladium-catalysed dealkoxylation ofN-alkoxyamides has been developed. This reaction proceeded smoothly with a range ofN-alkoxyamides in the absence of an external reductant, thereby establishing a convenient and reductant-free protocol. In addition, a gram-scale reaction could be achieved. Preliminary mechanistic investigations indicated that β-hydrogen elimination from a palladium alkoxide intermediate generated an intramolecular hydride source.
Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
, p. 11823 - 11838 (2019/10/02)
Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.