1. One-Pot Regioselective Synthesis of 2,6,9-Trisubstituted Adenines
- Author
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Alice Dias, L. Miguel Conde, Nádia Senhorães, M. Fernanda R. P. Proença, and Universidade do Minho
- Subjects
purine ,heterocycles ,0303 health sciences ,cyclization ,Science & Technology ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Organic Chemistry ,Regioselectivity ,ring closure ,01 natural sciences ,imidazole ,3. Good health ,0104 chemical sciences ,03 medical and health sciences ,One pot reaction ,Purine derivative ,ring opening ,030304 developmental biology ,Adenine derivatives - Abstract
A series of 2,6,9-substituted adenines were obtained from the easily accessible 5-amino-4-cyanoformimidoyl imidazoles 1, acetic and benzoic anhydrides and primary alkyl amines in a three-steps sequence. Acylation of 1 followed by addition of the amine led to the intermediates 5-amino-4-(N-acyl)formamidino imidazoles 4/5, under mild conditions. Cyclization of 4/5 under reflux in ethanol led to the desired substituted adenine. A preliminary stepwise study led to the development of three general and efficient one-pot methods for the synthesis of adenine derivatives. The one-pot three-step reaction in the presence of DMAP was the most convenient syn-thetic approach., The authors gratefully acknowledge the financial support by the University of Minho and Fundacao para a Ciencia e Tecnologia.
- Published
- 2011
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