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Synthesis of a New Class of Highly Functionalised Benzamides by Threefold Sequential Nucleophilic Substitution at a Resin‐Bound Polyelectrophile
Author(s) -
Grimstrup Marie,
Zaragoza Florencio
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200109)2001:17<3233::aid-ejoc3233>3.0.co;2-g
Subject(s) - chemistry , nucleophilic substitution , substitution (logic) , nucleophilic aromatic substitution , combinatorial chemistry , stereochemistry , class (philosophy) , organic chemistry , programming language , artificial intelligence , computer science
We have developed a solid‐phase synthesis of a new class of highly substituted and functionalised benzamides. This synthesis is based on the sequential introduction of three different nucleophiles at a resin‐bound 4,5‐difluoro‐2‐nitrobenzamide. After displacement of one fluorine atom by a thiol and oxidation to a sulfone, the remaining fluorine atom and the nitro group could be substituted sequentially by two different, aliphatic amines. In each of the three nucleophilic substitutions it was possible to use unprotected functionalised nucleophiles, giving fast and easy access to libraries of small organic molecules featuring polar functional groups such as hydroxy, amino, and ester groups and various heterocycles.