Annulation of primary amines to piperazines and diazaspirocycles utilizing α-methyl benzyl resin

Calum Macleod; Blanca I. Martinez-Teipel; William M. Barker; Roland E. Dolle

doi:10.1021/cc050106w

Annulation of primary amines to piperazines and diazaspirocycles utilizing α-methyl benzyl resin

Calum Macleod
, Blanca I. Martinez-Teipel
, William M. Barker
, Roland E. Dolle

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

Abstract

The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro-[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates 12, 17, and 22. Critical to the success of this chemistry was the development of α-methyl benzyl carbamate resin linker. This resin permits the cleavage of the heterocycles under mildly acidic conditions, free of contaminating linker-derived N-alkylated byproducts.

Original language	English
Pages (from-to)	132-140
Number of pages	9
Journal	Journal of combinatorial chemistry
Volume	8
Issue number	1
DOIs	https://doi.org/10.1021/cc050106w
State	Published - Jan 2006

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abstract = "The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro-[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates 12, 17, and 22. Critical to the success of this chemistry was the development of α-methyl benzyl carbamate resin linker. This resin permits the cleavage of the heterocycles under mildly acidic conditions, free of contaminating linker-derived N-alkylated byproducts.",

author = "Calum Macleod and Martinez-Teipel, \{Blanca I.\} and Barker, \{William M.\} and Dolle, \{Roland E.\}",

year = "2006",

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AU - Macleod, Calum

AU - Martinez-Teipel, Blanca I.

AU - Barker, William M.

AU - Dolle, Roland E.

PY - 2006/1

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N2 - The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro-[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates 12, 17, and 22. Critical to the success of this chemistry was the development of α-methyl benzyl carbamate resin linker. This resin permits the cleavage of the heterocycles under mildly acidic conditions, free of contaminating linker-derived N-alkylated byproducts.

AB - The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro-[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates 12, 17, and 22. Critical to the success of this chemistry was the development of α-methyl benzyl carbamate resin linker. This resin permits the cleavage of the heterocycles under mildly acidic conditions, free of contaminating linker-derived N-alkylated byproducts.

UR - https://www.scopus.com/pages/publications/31544433452

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JF - Journal of combinatorial chemistry

IS - 1

ER -

Annulation of primary amines to piperazines and diazaspirocycles utilizing α-methyl benzyl resin

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