The first synthesis of cyclic α‐amino phosphonic acid amides bearing the benzodiazaphosphorinanone system

Gröger, Harald; Wilken, J.; Martens, Jürgen; Neda, Ion; Schmutzler, Reinhard

doi:10.1002/(sici)1098-1071(1998)9:7<679::aid-hc13>3.0.co;2-#

Cited by 13 publications

(1 citation statement)

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“…The antibacterial activities of benzologues 141 149 were evaluated and found effective against Gram-positive and Gramnegative bacteria at different concentrations [75]. The hybrid derivatives 150 or 151, involving thiazolidine (150) or benzothiazine (151) and a benzodiazaphosphorinanone moiety in the same molecule can be valuable model compounds for research into new pharmaceuticals [76].…”

Section: Meomentioning

confidence: 97%

6-Membered P-Heterocycles: Ring-Condensed 1,3,2-Diheterophosphorinane 2-Chalcogenides

Frank¹,

Wölfling²

2007

COC

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Literature publications (up to the end of 2006) relating to the synthesis, biological significance and conformational behaviour of carbocycle-and heterocycle-condensed six-membered tetracoordinate P(V) 1,3,2-diheterophosphorinanes are reviewed. The replacement of carbon atoms of cyclohexane by P and O and/or N to form 1,3,2-dioxa-, 1,3,2-oxaza-or 1,3,2-diazaphosphorinanes introduces lone pair electrons instead of hydrogens and changes the bond angles and bond lengths, and can thereby lead to significantly different stereostructural preferences of the hetero ring as compared with those of cyclohexane. Although monocyclic 1,3,2-diheterophosphorinanes often exist in a chair conformation in both the solid and solution states, the existence of conformations other than a chair can predominate in some cases for steric and stereoelectronic reasons associated with the presence of bulky groups on the P-containing ring or in polycyclic rigid systems.After a brief account on the most important pharmacological and stereochemical features, involving the configuration assignment and conformation determination of P-diheterophosphorinanes, the present review mainly focuses on the synthesis and stereostructural studies of carbo-and heterocycle-condensed derivatives, where the fused ring may exert considerable effects on the conformational behaviour of the P-hetero ring.

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Section: Meomentioning

confidence: 97%