Abdollah Javidan, Mohammad Javad Taghizadeh and Khosrow Jadidi

Department of Chemistry, Imam Hossein University, Tehran, Iran

Abstract:

Some spiropyrrolidines are potential antileukemic and anticonvulsant agents [1] and possess antiviral [2] and local anaesthetic [3] activities. In this paper we will report asymmetric 1,3-dipolar cycloaddition reaction of the dipolarophiles 1 and azomethine ylides to give the novel spiro pyrrolo/pyrrolizidinos  instead of  bis- spirooxindolopyrrolizidines. Condensation of compounds 2 and 3 after decarboxylation leading to the non-stabilized azomethine ylides stereogenic centers in one step. We expected by this method a bis spirooxindolopyrrolizidine 5 and 8 prepared.  But by using this strategy only diastereoisomers 4  and 7 were obtained The structures of cycloaddition products 5 were assigned by IR, 1HNMR, 13CNMR, Mass spectral data and single crystal X-ray analysis (Fig. 1).

 

Refrences

[1]        M. A. Abou-Gharbia and P. H. Doukas, Heterocycles.,  1979, 12, 637–640.
[2]        K. Lundahl, J. Schut, J. L. M. A. Schlatmann, G. B. Paerels and A. Peters, J. Med. Chem. 1972, 15, 129–132.
[3]        M. J. Kornet and A. P. Thio, J. Med. Chem. 1976, 19, 892– 898.