Heterocyclizations with Tosylmethyl Isocyanide Derivatives. A New Approach to Substituted Azolopyrimidines
- 13 May 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (12) , 4879-4882
- https://doi.org/10.1021/jo050029r
Abstract
An efficient synthesis of substituted azolopyrimidines such as pyrido[3‘,2‘:4,5]pyrrolo[1,2-c]pyrimidines, pyrimido[1,6-a]indoles, benzo[4,5]imidazo-[1,2-c]pyrimidines, an imidazo[1,2-c]pyrimidine, and pyrazolo[1,5-c]pyrimidines is described. The method involves the reaction of N-protected bromomethylazoles and tosylmethyl isocyanide (TosMIC) derivatives in nonanhydrous media. The study of the reaction conditions shows that the method is only successful under phase-transfer conditions (CH2Cl2/30% aq NaOH) using benzyltriethylammonium chloride as a catalyst.Keywords
This publication has 9 references indexed in Scilit:
- Reaction of Bromomethylazoles and Tosylmethyl Isocyanide. A Novel Heterocyclization Method for the Synthesis of the Core of Marine Alkaloids Variolins and Related AzolopyrimidinesThe Journal of Organic Chemistry, 2004
- Reaction of 2-Bromomethylazoles and TosMIC: A Domino Process to Azolopyrimidines. Synthesis of Core Tricycle of the Variolins AlkaloidsOrganic Letters, 2000
- An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents1The Journal of Organic Chemistry, 2000
- Pyrrolodiazines. 5. Synthesis, Structure, and Chemistry of Pyrrolo[1,2-c]pyrimidine. Dipolar Cycloaddition of Pyrrolo[1,2-c]pyrimidinium YlidesThe Journal of Organic Chemistry, 1999
- p-Tolysulfonylmethyl Isocyanide (TosMIC) - a versatile formaldehyde equivalent with reversed polarityAdvanced Synthesis & Catalysis, 1998
- Improved synthesis of pyrrolo[1,2-c]pyrimidine and derivativesTetrahedron Letters, 1996
- Alkaloids from the antarctic sponge Kirkpatrickia varialosa.Tetrahedron, 1994
- Chemistry of sulfonylmethyl isocyanides. 37. Synthesis of 3,4-disubstituted pyrroles bearing substituents of electron-withdrawing and/or electron-donating natureThe Journal of Organic Chemistry, 1992
- Chemistry of sulfonylmethyl isocyanides. 12. Base-induced cycloaddition of sulfonylmethyl isocyanides to carbon,nitrogen double bonds. Synthesis of 1,5-disubstituted and 1,4,5-trisubstituted imidazoles from aldimines and imidoyl chloridesThe Journal of Organic Chemistry, 1977