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Reductive Transformations of Polyfunctional Nitro Compounds: Synthesis of Methyl 7‐Aminoalkanoates and Five‐Membered Cyclic Nitrones ‐ Inter‐ and Intramolecular 1,3‐Dipolar Cycloadditions
Author(s) -
Zschiesche Ruth,
Reißig HansUlrich
Publication year - 1989
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.198919890197
Subject(s) - chemistry , nitrone , intramolecular force , cycloaddition , acrylonitrile , nitro , ammonium formate , 1,3 dipolar cycloaddition , nitrile , organic chemistry , medicinal chemistry , acetonitrile , catalysis , polymer , alkyl , copolymer
Using ammonium formate and Pd/C, acetals 1 and 3 are converted into the amines 2 and 4 , respectively, whereas unprotected nitro ketones as 5, 7, 9 , and 11 furnish five‐membered nitrones in good yields. With these nitrones 1,3‐dipolar cycloadditions to acrylonitrile and trimethyl(vinyl)silane are described. The regio‐chemistry of these reactions, giving mixtures of 5‐substituted and 4‐substituted isoxazolidines in most cases, can be explained by the frontier‐orbital model. One example of an intramolecular nitrone cycloaddition ( 27 → 28 ) demonstrates the potential of this approach for construction of polycyclic compounds.