Convenient Synthesis of Mono- And Ditosylated 1,4,7-Triazacyclononane

Lázár, István; Takács, Zoltán

doi:10.1081/scc-100105889

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2002

2023

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Cited by 4 publications

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“…In typical approaches to NO(R 1 ,R 1 ,H) and NO(R 2 ,H,H), 1-fold and 2-fold protected tacn occur, respectively. Reported are the 1-fold protection of tacn with tert -butyloxycarbonyl (Boc), , benzyloxycarbonyl (Cbz), trityl, and tosyl, as well as through a temporary attachment to a resin, , and the 2-fold protection of tacn with Boc, ,, Cbz, trityl, trifluoroacetyl (tfAc), , and tosyl, as well as through the conversion of tacn into an aminal . Fitting in these approaches, the synthesis of NO(R 1 ,R 2 ,H) via NO(Boc,Cbz,H) was realized .…”

Section: Introductionmentioning

confidence: 99%

Equipping 1,4,7-Triazacyclononane with Substituents via Solid-Phase Synthesis

Ossadnik,

Voss,

Godt

2023

J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Equipping 1,4,7-Triazacyclononane with Substituents via Solid-Phase Synthesis

Ossadnik,

Voss,

Godt

2023

J. Org. Chem.

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ChemInform Abstract: Convenient Synthesis of Mono‐ and Ditosylated 1,4,7‐Triazacyclononane

Lázár¹,

Takács²

2002

ChemInform

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Synthesis of Previously Inaccessible Derivatives of 1,4,7‐Tri‐R‐1,4,7‐Triazacyclononane, Including Chiral Examples, and a Rapid Synthesis of the HCl Salts of H₃tacn and H₄dtne

et al. 2018

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The synthesis of 1,4‐di‐tert‐butyl‐7‐R‐1,4,7‐triazacyclononane (tBu2Rtacn) derivatives through a “crab‐like” cyclization is reported. The tert‐butyl groups were cleavable with concentrated hydrochloric acid, allowing for a facile and convenient synthesis of the HCl salt of H3tacn and the most direct route to its industrially relevant binucleating N‐ethylene bridged derivative, H4dtne. In addition, the synthesis of chiral tacn derivatives with both one and two stereocenters in non‐annulet, alpha‐N positions is reported.

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Convenient Synthesis of Mono- And Ditosylated 1,4,7-Triazacyclononane

Cited by 4 publications

References 6 publications

Equipping 1,4,7-Triazacyclononane with Substituents via Solid-Phase Synthesis

Equipping 1,4,7-Triazacyclononane with Substituents via Solid-Phase Synthesis

ChemInform Abstract: Convenient Synthesis of Mono‐ and Ditosylated 1,4,7‐Triazacyclononane

Synthesis of Previously Inaccessible Derivatives of 1,4,7‐Tri‐R‐1,4,7‐Triazacyclononane, Including Chiral Examples, and a Rapid Synthesis of the HCl Salts of H₃tacn and H₄dtne

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Convenient Synthesis of Mono- And Ditosylated 1,4,7-Triazacyclononane

Cited by 4 publications

References 6 publications

Equipping 1,4,7-Triazacyclononane with Substituents via Solid-Phase Synthesis

Equipping 1,4,7-Triazacyclononane with Substituents via Solid-Phase Synthesis

ChemInform Abstract: Convenient Synthesis of Mono‐ and Ditosylated 1,4,7‐Triazacyclononane

Synthesis of Previously Inaccessible Derivatives of 1,4,7‐Tri‐R‐1,4,7‐Triazacyclononane, Including Chiral Examples, and a Rapid Synthesis of the HCl Salts of H3tacn and H4dtne

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Product

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Synthesis of Previously Inaccessible Derivatives of 1,4,7‐Tri‐R‐1,4,7‐Triazacyclononane, Including Chiral Examples, and a Rapid Synthesis of the HCl Salts of H₃tacn and H₄dtne