Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 31, Pages 5980-5988Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000955
Keywords
Nitrogen heterocycles; aza-Henry reaction; nitro-Mannich reaction; Nitroalkanes
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Funding
- University of Sydney [LO961 U3298]
- School of Chemistry at the University of Sydney
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The aza-Henry reaction of 3,4-dihydroisoquinoline is reported. The reaction is favourable in excess nitromethane under ambient conditions. Isolation of the unstable reaction product is achieved by acylation or alkylation, allowing the synthesis of Reissert-like compounds in good yields from a one-pot, three-component coupling. The rates of reaction for dihydroisoquinoline and the corresponding benzylisoquinolinium ion have been investigated in the presence and absence of base. The reaction with dihydroisoquinoline probably proceeds via an azinic acid tautomer of nitromethane, a reaction pathway unavailable to the isoquinolinium ion. The traditionally problematic reduction of two of the resulting beta-nitroamine derivatives was achieved, providing access to a number of new chiral vicinal diamines.
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