Solid-phase synthesis of N,N′ substituted guanidines☆
A variety of alcohols react with resin-bound N,N′-bis(t-butoxycarbonyl)thiopseudourea under Mitsunobu conditions to give the corresponding alkylated thiopseudoureas. The protected guanidines are liberated from the resin upon exposure to ammonia or primary amines.
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Guanidines from 'toxic substances' to compounds with multiple biological applications - Detailed outlook on synthetic procedures employed for the synthesis of guanidines
2015, Bioorganic ChemistryCitation Excerpt :In 2001, Christoph W. Zapf and group also reported the development of a solid support-linked guanidinylating reagent. This reagent consists of a urethane-protected triflyl guanidine, attached to the resin via a carbamate linker (Scheme 57) [85]. The general concept of tethered combinatorial libraries of compounds in which two pharmacophores are found, was described by Houghten and group in 2001.
A facile and practical one-pot 'catch and release' synthesis of substituted guanidines
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2009, Bioorganic and Medicinal Chemistry LettersThiol on silica as a 'catch and release' support for isocyanates to afford ureas
2007, Tetrahedron LettersMicrowave-assisted solid phase synthesis of Imatinib, a blockbuster anticancer drug
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Presented in part (by OBW) at IBC's Fifth Annual International Symposium “Peptidomimetics & Small Molecule Design,” March 5–6, 1998, Philadelphia, PA.