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An Original Traceless Linker Strategy for Solid‐Phase Synthesis of N , N′ , N″ ‐Substituted Guanidines
Author(s) -
Gomez Laurent,
Gellibert Françoise,
Wagner Alain,
Mioskowski Charles
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20001103)6:21<4016::aid-chem4016>3.0.co;2-w
Subject(s) - guanidine , amine gas treating , linker , chemistry , solid phase synthesis , nucleophile , electrophile , combinatorial chemistry , yield (engineering) , toluene , sequence (biology) , primary (astronomy) , organic chemistry , catalysis , materials science , peptide , computer science , biochemistry , physics , astronomy , metallurgy , operating system
An original sequence for solution‐ and solid‐phase synthesis of N , N′ , N″ ‐trisubstituted guanidines is described. The sequence involves as key intermediate a bis‐electrophilic chlorothioformamidine that is stable, easy to prepare and also easy to handle. Supported chlorothioformamidine, prepared in two steps from Merrifield resin, undergoes smooth nucleophilic addition of a primary amine to afford the corresponding supported isothiourea. The guanidine is obtained in satisfactory yield and good purity through a functionalizing‐release process by heating the supported isothiourea in the presence of a primary amine in toluene at 100 °C. Compatibility of this sequence with several functional groups is demonstrated.