Zur Umlagerung von Azidomalonestern | Zendy

Frank Jürgen | Zendy; Stoll Gerhard | Zendy; Musso Hans | Zendy

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Zur Umlagerung von Azidomalonestern

Author(s) -

Frank Jürgen,

Stoll Gerhard,

Musso Hans

Publication year - 1986

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.198619861118

Subject(s) - chemistry , malonate , isopropyl , hydrolysis , medicinal chemistry , photodissociation , alkyl , nitrogen , malonic acid , organic chemistry

Rearrangement of Azidomalonic Esters Dimethyl azido[6‐(methoxycarbonyl)‐2‐oxo‐2 H ‐pyran‐4‐ylmethyl]malonate ( 4 ) is photolyzed under loss of nitrogen and rearrangement of one methoxycarbonyl group to form the mixture of Z und E isomers of the α,β‐unsaturated amino acid esters 8 and 9 . On photolysis of isopropyl‐ and isobutylazidomalonates 10 migration of the alkyl group is observed exclusively. The (alkylimino)malonates 14 so formed have been hydrogenated and hydrolyzed to give the N ‐alkylglycine derivatives 16 .

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