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Tandem Ugi MCR/Mitsunobu Cyclization as a Short, Protecting‐Group‐Free Route to Benzoxazinones with Four Diversity Points
Author(s) -
Banfi Luca,
Basso Andrea,
Giardini Lorenzo,
Riva Renata,
Rocca Valeria,
Guanti Giuseppe
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001077
Subject(s) - chemistry , tandem , mitsunobu reaction , stereospecificity , functional group , ugi reaction , combinatorial chemistry , protecting group , stereochemistry , organic chemistry , catalysis , isocyanide , materials science , polymer , composite material , alkyl
A tandem Ugi/Mitsunobu protocol, starting from o ‐aminophenols, α‐hydroxy acids, amines and aldehydes gives benzo[ b ][1,4]oxazin‐3‐ones of general formula 1 in two high‐yielding steps, with the introduction of up to four diversity inputs. The mildness of the methodology allows the stereospecific synthesis of enantiomerically pure products as well as the introduction of additional functional groups. The overall procedure can also be carried out in a one‐pot manner.