Events The 14th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 14th International Electronic Conference on Synthetic Organic Chemistry

Published date

30 Oct, 2010

Citation

Dmitry A. Cheshkov, Anastasia A. Fesenko, Anatoly D. Shutalev, Base-Promoted Cascade Transformation of Tetrahydropyrimidinones into Novel Tricyclic bis-Diazepinones, in Proceedings of The 14th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2010, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-14-00457

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Base-Promoted Cascade Transformation of Tetrahydropyrimidinones into Novel Tricyclic bis-Diazepinones

Dmitry A. Cheshkov ¹

Anastasia A. Fesenko ¹

Anatoly D. Shutalev ¹

1. Department of Organic Chemistry, Moscow State Academy of Fine Chemical Technology, 86 Vernadsky Ave., 119571 Moscow, Russian Federation

Abstract

In the presence of strong bases (NaH, DBU, KOH), ethyl 4-chloromethyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate and 4-mesyloxymethyl-6-methyl-5-tosyl-1,2,3,4-tetrahydropyrimidin-2-one are transformed into novel tricyclic compounds, diethyl 9-methyl-5-methylene-3,11-dioxo-2,3,4,5,6a,7,10,11-octahydro-1,6-methano[1,3]diazepino[1,7-e][1,3,5]-triazocine-6,8(1H)-dicarboxylate and 9-methyl-5-methylene-6,8-ditosyl-1,2,4,5,6,6a,7,10-octahydro-1,6-methano[1,3]diazepino[1,7-e][1,3,5]triazocine-3,11-dione, respectively.

Keywords

Two Pathways for the Reaction of Ethyl 4-Chloromethyl-6-methyl- 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate with Thiophenolates: Ring Expansion versus Nucleophilic Substitution

One-pot three-component Mannich-type reaction catalyzed by functionalized ionic liquid