2013
DOI: 10.1002/hc.21086
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α‐Aminophosphonates and α‐Aminophosphine Oxides by the Microwave‐Assisted Kabachnik–Fields Reactions of 3‐Amino‐6‐methyl‐2 H‐pyran‐2‐ones

Abstract: The microwave‐assisted Kabachnik–Fields reaction of a series of 3‐amino‐6‐methyl‐2H‐pyran‐2‐ones, paraformaldehyde, and dialkyl phosphites or diphenylphosphine oxide led to α‐aminophosphonates or α‐aminophosphine oxides, respectively. The α‑aminophosphonates were obtained under solvent‐free conditions, whereas the α‑aminophosphine oxides in acetonitrile. The novel products were characterized by NMR and mass spectral data. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:221–225, 2013; View this article online… Show more

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Cited by 33 publications
(18 citation statements)
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“…A few N-(2H-pyranonyl)-α-aminophosphonates or -α-aminophosphine oxides were also synthesized starting from 3-amino-2H-pyran-2-one derivatives [30,31]. Double "phospha-Mannich" condensations were also developed applying two equivalents of the formaldehyde and the >P(O)H species to one equivalent of the primary amine (Scheme 3) [32][33][34].…”
Section: Methodsmentioning
confidence: 99%
“…A few N-(2H-pyranonyl)-α-aminophosphonates or -α-aminophosphine oxides were also synthesized starting from 3-amino-2H-pyran-2-one derivatives [30,31]. Double "phospha-Mannich" condensations were also developed applying two equivalents of the formaldehyde and the >P(O)H species to one equivalent of the primary amine (Scheme 3) [32][33][34].…”
Section: Methodsmentioning
confidence: 99%
“…Then 3-amino-6-methyl-2H-pyran-2-ones (56) were utilized in the KabachnikFields reaction with formaldehyde and dialkyl phosphites or diphenylphosphine oxide (Scheme 3.39) [75].…”
Section: The Addition Of >P(o)h Species To Carbonyl-compoundsmentioning
confidence: 99%
“…In another version, amino-2H-pyran-2-ones (53) were used as the starting materials to afford interesting N-heterocyclic α-aminophosphonates or α-aminophosphine oxides (54) (Scheme 19) [72,73].…”
Section: Kabachnik-fields Reactionsmentioning
confidence: 99%