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Synthesis and Reactivity of Imines Derived from Bisphosphonates and 3-Phosphorylated 2-Aza-1,3-dienes

✍ Scribed by Francisco Palacios; Marie J Gil; Eduardo Martı́nez de Marigorta; Marta Rodrı́guez

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
201 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐThe synthesis and some reactions of imines derived from aminoalkylbisphosphonates and 2-aza-1,3-butadienes is described. Bisphosphonylalkylimino compounds are useful intermediates in the preparation of aminoalkylbisphosphonate derivatives by reduction of the imino linkage with sodium triacetoxyborohydride as well as in the synthesis of 2-aza-1,3-butadienes by an ole®nation reaction. The electrocyclization of phosphorylated 2-aza-1,3,5-trienes afforded substituted 2-phosphorylated pyridines.

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Synthesis of 3-phosphorylated 2-aza-1,3-
Synthesis of 3-phosphorylated 2-aza-1,3-dienes from imines derived from bisphosphonates
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A synthesis of 2-aza-l,3-butadienes 3 substituted with a phosphonate group in the 3-position is described. The key step is the olefination reaction of bisphosphonylalkyl imino compounds 2, with aldehydes in the presence of base. Heterocyclisation of 2-azatrienes 5 afforded substituted 2-phosphorylat

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