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Highly efficient Synthesis of per-substituted amino-cyclodextrins under Microwave Irradiation in a closed Cavity

Published online by Cambridge University Press:  18 February 2013

Giancarlo Cravotto ,
Katia Martina ,
Marina Caporaso ,
Georgios Heropoulos  and
László Jicsinszky
Giancarlo Cravotto*
Affiliation:
Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via P. Giuria 9, 10125 Torino, Italy.
Katia Martina
Affiliation:
Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via P. Giuria 9, 10125 Torino, Italy.
Marina Caporaso
Affiliation:
Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via P. Giuria 9, 10125 Torino, Italy.
Georgios Heropoulos
Affiliation:
Institute of Organic and Pharmaceutical Chemistry, The National Hellenic Research Foundation, 11635 Athens, Greece.
László Jicsinszky
Affiliation:
Cyclolab R&D Laboratory, Illatos út 7, H-1097 Budapest, Hungary.
*
*Author for correspondence: E-mail: [email protected]; FAX +39.011.6707687
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Abstract

Synthetic chemists are paying ever more attention to enabling technologies as a means to opening the paths towards the double goal of achieving high efficiency and meeting green criteria. Non-conventional techniques that create unique environments which promote selective modification have been investigated by many as part of the search for more highly efficient synthetic derivatization of cyclodextrins (CD). A few optimized microwave-assisted protocols have so far been developed for the preparation of selective per-alkylated aminocyclodextrin. In this work, a series of β-CD derivatives, whose primary hydroxyls were all replaced by amino groups, has efficiently been synthesized from per-(6-iodo-6-deoxy)-β-CD via nucleophilic substitution with amines under microwave irradiation in closed vessel (N2 pressure). The reduction of per-(6-azido-6-deoxy)-β-CD to per-(6-amino-6-deoxy)-β-CD via catalytic hydrogenation has also been successfully carried out under dielectric heating.

Keywords

microwave heatingchemical synthesischemical substitution
Type
Articles
Information
MRS Online Proceedings Library (OPL) , Volume 1492: Symposium D/G – Materials for Sustainable Development—Challenges and Opportunities , 2013 , pp. 177 - 182
Copyright
Copyright © Materials Research Society 2013 

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