Stereoselective One-Pot Synthesis of Functionalised Phosphonates by Three-Component Reaction between Trimethylphosphite,Dialkyl Acetylenedicarboxylates and Aldehyde Semicarbazones

Abstract

Three-component reaction between dialkyl acetylenedicarboxylates, trimethylphosphite, and aldehyde semicarbazones leads to functionalised phosphonates in good yields.

Keywords

acetylenic esters semicarbazones phosphonates trimethylphosphite

References

Corbridge

D.E.C.

, Phosphorus an outline of the chemistry, biochemistry, and uses 5th edn. Elsevier, Amsterdam, 1995.

Engel

, Synthesis of Carbon–phosphorus bonds, CRC Press, Boca Raton, FL, 1988.

Kolodiazhnyi

O.I.

, Russ. Chem. Rev., 1997, 66, 225.

Bestmann

H.J.

, and Zimmermann

, Top. Curr. Chem., 1983, 109, 85.

Maryano

B.E.

, and Reits

A.B.

, Chem. Rev., 1989, 89, 863.

Pietrusiewiz

K.M.

, and Zablocka

, Chem. Rev., 1994, 94, 1375.

Tebby

J.C.

, in Phosphorus-31 NMR spectroscopy in stereochemical analysis, Verkede

J.C.

, and Quin

L.D.

(eds), VCH, Weinheim, 1987 ch. 1, pp. 1–60.

George

M.V.

, Khetan

S.K.

, and Gupta

R.K.

, Adv. Heterocycl. Chem., 1976, 19, 354.

Yavari

, and Anary-Abbasinejad

, Org. Biomolec. Chem., 2003, 3, 560.

10.

Karplus

, J. Am. Chem. Soc., 1963, 88, 2870.

11.

Haasnot

C.A.G.

, De Leeuww

F.A.A.M.

, and Altona

, Tetrahedron, 1980, 36, 2783.

12.

Breitmaier

, and Voelter

, Carbon-13 NMR spectroscopy, 3rd edn., VCH, New York, 1990, p. 250.