A novel facile solid-phase strategy for the synthesis of N, N', N?-substituted guanidines (original) (raw)

TFA-Sensitive Arylsulfonylthiourea-Assisted Synthesis of N,N‘-Substituted Guanidines

The Journal of Organic Chemistry, 2003

An efficient synthesis of N,N′-substituted guanidine derivatives was developed via an aromatic sulfonylactivated thiourea intermediate. The use of certain aromatic sulfonamides, such as PbfNH 2 , as the key reagent to incorporate a TFA-labile guanidine protection group greatly facilitates solid-phase synthesis of N,N′-substituted guanidine compounds.

Synthesis of guanidine from ammonium thiocyanate in solid state

Journal of the Brazilian …, 2004

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N,N′,N″-Tri-Boc-guanidine (TBG): a common starting material for both N-alkyl guanidines and amidinoureas

Tetrahedron Letters, 2007

In this Letter, we describe the unexpected reaction pattern of N,N 0 N 00-tri-Boc-guanidine (TBG) with amines at room temperature and under reflux conditions affording N-substituted guanidines and amidinoureas, potentially important compounds with extensive applications in medicinal chemistry. This investigation shows that TBG is an excellent, readily available common starting material for the synthesis of various N-alkyl guanidines as well as N-alkyl-N 0-substituted amidinoureas by simply manipulating the reaction conditions.

Synthesis of N-acridinyl-N′-alkylguanidines: Dramatic influence of amine to guanidine replacement on the physicochemical properties

Bioorganic & Medicinal Chemistry Letters, 2008

Transformation of aminoacridines into N-acridinyl-N 0 -alkylguanidines is described. The chosen procedure allows introduction of pendent substituents (exemplified by N,N-dimethylaminopropyl chain) into key acridinyl thioureas, thus opening the way to structural diversity. Spectroscopic study and pK a determination show that the presence of the strongly basic guanidine has a dramatic influence on the ionization of the acridine nucleus by lowering the pk a value down to 4.49.

Synthesis and applications of C2-symmetric guanidine bases

Tetrahedron Letters, 2003

The preparation of the tetracyclic C 2 -symmetric guanidinium salts 5 and 11-13 is reported together with their application to enantioselective transformations. Scheme 1. Reagents and conditions: (a) TBDMSCl/imid (99%); (b) DIBAL-H (95%); (c) TosCl/Py (85%); (d) NaI/acetone (89%); (e) i. CH 3 COCHPPh 3 /nBuLi, ii. aq. CH 2 O (79%); (f) i. guanidine/DMF, ii. HCl/MeOH, iii. NaBF 4 (aq.) (44%).