Abstract
Different N-protected dichloromethanimines have been used for the preparation of pyrido[3 ,2 :4,5]pyrrolo[1,2-c]pyrimidines and the results are compared. The preparation of 4chloro-9-tosylaminopyrido[3 ,2 :4,5]pyrrolo[1,2-c]pyrimidine is described.
Highlights
The synthesis of variolin B 1 1 and derivatives has been one of the important topics developed in our laboratory during the last years.[2]
Our previous synthetic procedure described for the preparation of deoxyvariolin B 2 is based on the construction of the tricyclic system of pyrido[3 ́,2 ́:4,5]pyrrolo[1,2-c]pyrimidone, followed by the transformation of the pyrimidone C ring into an N-protected-aminopyrimidine, halogenation at position 5 of the tricyclic system and a palladium cross-coupling reaction for the introduction of the fourth heteroaromatic D ring (Scheme 1)
In this paper we describe the use of dichloromethanimine with different N-protecting/blocking groups 3a-e for the construction of the properly fuctionalized and protected aminopyrimidine ring C of variolin B and derivatives
Summary
The synthesis of variolin B 1 1 and derivatives has been one of the important topics developed in our laboratory during the last years.[2]. Abstract Different N-protected dichloromethanimines have been used for the preparation of pyrido[3 ́,2 ́:4,5]pyrrolo[1,2-c]pyrimidines and the results are compared. With the elimination of the O-protecting group, the resulting alcohols 8a-b and 9a-b gave assignable 1H NMR spectra, with the disappearance of the second chiral centre.
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