Reaction of 2-bromomethylazoles and TosMIC: A domino process to azolopyrimidines. Synthesis of core tricycle of the variolins alkaloids

J Mendiola; J M Minguez; J Alvarez-Builla; J J Vaquero

doi:10.1021/ol0062087

Reaction of 2-bromomethylazoles and TosMIC: A domino process to azolopyrimidines. Synthesis of core tricycle of the variolins alkaloids

Org Lett. 2000 Oct 19;2(21):3253-6. doi: 10.1021/ol0062087.

Authors

J Mendiola¹, J M Minguez, J Alvarez-Builla, J J Vaquero

Affiliation

¹ Departamento de Química Orgánica, Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, Spain.

PMID: 11029183
DOI: 10.1021/ol0062087

Abstract

A new reaction of N-protected 2-bromomethylazoles and tosylmethyl isocyanide (TosMIC) leading to the preparation of azolopyrimidines is described. This domino sequence was used to synthesize the pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine core of alkaloids variolins from 4-methoxy-2-methylpyrrolo[2,3-b]pyrimidine in two steps.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry*
Azoles / chemistry*
Pyrimidines / chemical synthesis*
Tosyl Compounds / chemistry*

Substances

Alkaloids
Azoles
Pyrimidines
Tosyl Compounds