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Vugts DJ, Koningstein MM, Schmitz RF, et al. Multicomponent synthesis of dihydropyrimidines and thiazines. Chemistry. 2006;12(27):7178-89doi: 10.1002/chem.200600168.
Vugts, D. J., Koningstein, M. M., Schmitz, R. F., de Kanter, F. J., Groen, M. B., & Orru, R. V. (2006). Multicomponent synthesis of dihydropyrimidines and thiazines. Chemistry (Weinheim an der Bergstrasse, Germany), 12(27), 7178-89. https://doi.org/10.1002/chem.200600168
Vugts, Danielle J, et al. "Multicomponent synthesis of dihydropyrimidines and thiazines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 12,27 (2006): 7178-89. doi: https://doi.org/10.1002/chem.200600168
Vugts DJ, Koningstein MM, Schmitz RF, de Kanter FJ, Groen MB, Orru RV. Multicomponent synthesis of dihydropyrimidines and thiazines. Chemistry. 2006 Sep 18;12(27):7178-89. doi: 10.1002/chem.200600168. PMID: 16847990.
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Chemistry. 2006 Sep 18;12(27):7178-89. doi: 10.1002/chem.200600168.

Multicomponent synthesis of dihydropyrimidines and thiazines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Danielle J Vugts, Manoe M Koningstein, Rob F Schmitz, Frans J J de Kanter, Marinus B Groen, Romano V A Orru

Affiliations

  1. Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.

PMID: 16847990 DOI: 10.1002/chem.200600168

Abstract

A broad range of differently substituted dihydropyrimidines and thiazines can be efficiently prepared by using a four-component reaction between phosphonates, nitriles, aldehydes, and iso(thio)cyanates. The scope and limitations of this multicomponent reaction are fully described. Variation of all four components has been investigated. The nitrile and aldehyde inputs can be varied extensively, but variation of the phosphonate input remains limited. An interesting rearrangement leading to phosphoramidates has been observed. Furthermore, the multicomponent reaction seems to be restricted to the use of isocyanates with strongly electron-withdrawing substituents, but an interesting additional exchange reaction under microwave conditions leads to dihydropyrimidines with less electron-withdrawing substituents at N3. In addition, a diastereoselective formation of dihydropyrimidines has been observed when using a chiral aldehyde as the input. Finally, by changing the isocyanate component to an isothiocyanate, thiazines are efficiently formed instead of the corresponding thio-dihydropyrimidines.

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