Sage Journals: Discover world-class research

Abstract

Protonation of highly reactive 1,4-zwitterionic intermediate generated in the reaction between pyridine or isoquinoline and dialkyl acetylenedicarboxylates by strong CH-acid such as 1,1,1,5,5,5-hexafluoropentane-2,4-dione, leads to a vinyl pyridinium cation derivatives, which undergo carbon centred Michael type addition with the conjugate base of the CH-acid to produce highly functionalised stable 1,4-diionic nitrogen betaines.

Keywords

1,1,1,5,5,5-hexafluoropentane-2,4-dione pyridine;CH-acid isoquinoline zwitterionic intermediate 1,4-diionic nitrogen betaines

References

(a) Dikstein

J. I.

, and Miller

S. I.

, The Chemistry of Functional Groups. The Chemistry of Carbon-Carbon Triple Bond, Part 2, Chapter 19; Patai

, Ed.; Wiley: Chichester, 1978, p. 813.

Winterfeldt

, Angew. Chem., Int. Ed. Engl., 1967, 6, 423.

Acheson

R.M.

, and Elmore

N. F.

, Advances in Heterocyclic Chemistry, 1978, 23, 263 and references cited therin.

Acheson

R.M.

, and Woollard

, J. Chem. Soc., 1971, 3296.

Acheson

R.M.

, and Taylor

G. A.

, J. Chem. Soc., 1960, 1691.

Acheson

R.M.

, and Woollard

, J. Chem. Soc. Perkin Trans. I, 1975, 438.

Acheson

R.M.

, and Plunkett

A. O.

, J. Chem. Soc., 1964, 2676.

Crabtree

, Johnson

A. W.

, and Tebby

J. C.

, J. Chem. Soc., 1961, 3497.

Huisgen

, Morikawa

, Herbig

, and Brunn

, Chem. Ber., 1967, 100, 1094.

10.

LeGoff

, and LaCount

R. B.

, J. Org. Chem., 1964, 29, 423.

11.

Bamfield

, Crabtree

, and Johnson

A. W.

, J. Chem. Soc., 1965, 4355.

12.

Shaabani

, Teimouri

M. B.

, Yavari

, Norouzi Arasi

, and Bijanzadeh

H. R.

, J. Fluor. Chem., 2000, 103, 155.

13.

Shaabani

, Bazgir

, Soleimani

, and Bijanzadeh

H. R.

, J. Fluor. Chem., 2000, 116, 93.

14.

Yavari

, Shaabani

, Asghari

, Olmstead

M. M.

, and Safari

, J. Fluor. Chem., 1997, 86, 77.

15.

Yavari

, Anary-Abbasinejad

, and Alizadeh

, Monatsh. Chem., 2002, 133, 1331.

Reaction between Nitrogen–Containing Heterocycles and Dialkyl Acetylenedicarboxylate with Strong Ch-Acid: Synthesis of Stable Highly Functionalised 1,4-Diionic Nitrogen Betaines

Abstract

Keywords

References