title: A solution-phase parallel synthesis of alkylated guanidines from thioisocyanates and amines.
abstract: An efficient solution-phase parallel synthesis of alkylated guanidines from commercial thioisocyanates and amines is described. In the first step, a thioisocyanate reacts with one equivalent of ammonia or a primary or secondary amine to give a thiourea intermediate. The latter is S-alkylated with n-dodecyl bromide resulting in the corresponding thiouronium bromide. Finally, the reaction of the thiouronium salt with a second equivalent of ammonia or a primary amine yields an alkylated guanidine. All three synthetic steps are easily combined in a one-pot high-yielding procedure with a simple work-up. Ca. 250 guanidine derivatives with high structural and functional diversity were synthesized by the developed method. 35 representatives reported in this study were fully characterized.
authors: Enamine Ltd., 23 Alexandra Matrosova Street, Kiev, 01103, Ukraine.
authors: Andrey V
authors: AV
authors: Bogolubsky
authors: Alexander
authors: A
authors: Grishchenko
authors: Sergey E
authors: SE
authors: Pipko
authors: Anzhelika
authors: A
authors: Konovets
authors: Alexander
authors: A
authors: Chuprina
authors: Andrey
authors: A
authors: Tolmachev
authors: Alexander N
authors: AN
authors: Boyko
authors: Alexey
authors: A
authors: Chekotylo
authors: Oleg
authors: O
authors: Lukin
mesh_terms: D000588:Amines / Q000737:chemistry / Q000378:metabolism*; D002384:Catalysis; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D017953:Isocyanates / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure
chemical_list: D000588:Amines; D006146:Guanidines; D017953:Isocyanates
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