A New class of tröger's base analogues bearing spiro[4.5] lactone straps

Andrew B. Mahon; Donald C. Craig; Andrew C. Try

doi:10.1055/s-0028-1083341

A New class of tröger's base analogues bearing spiro[4.5] lactone straps

Andrew B. Mahon, Donald C. Craig, Andrew C. Try

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

8 Citations (Scopus)

Abstract

A protocol for the introduction of spiro[4.5] lactone straps onto the Troger's base scaffold has been developed. The conversion was found to be most efficient when an appropriate carboxylic acid derivative reacted with 5,6,11,12-tetrahydrodiben- zo[bf][1,5]diazocines. Whilst phthaloyl dichloride was the main strap-forming precursor used, other 1,2-unsaturated dicarboxylic acids could be used in the presence of N-N'-dicyclohexylcarbodiimide.

Original language	English
Pages (from-to)	636-642
Number of pages	7
Journal	Synthesis
Issue number	4
DOIs	https://doi.org/10.1055/s-0028-1083341
Publication status	Published - 2009

Keywords

Tröger’s base
lactones
amines
cyclization
spiro compounds

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10.1055/s-0028-1083341

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abstract = "A protocol for the introduction of spiro[4.5] lactone straps onto the Troger's base scaffold has been developed. The conversion was found to be most efficient when an appropriate carboxylic acid derivative reacted with 5,6,11,12-tetrahydrodiben- zo[bf][1,5]diazocines. Whilst phthaloyl dichloride was the main strap-forming precursor used, other 1,2-unsaturated dicarboxylic acids could be used in the presence of N-N'-dicyclohexylcarbodiimide.",

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AB - A protocol for the introduction of spiro[4.5] lactone straps onto the Troger's base scaffold has been developed. The conversion was found to be most efficient when an appropriate carboxylic acid derivative reacted with 5,6,11,12-tetrahydrodiben- zo[bf][1,5]diazocines. Whilst phthaloyl dichloride was the main strap-forming precursor used, other 1,2-unsaturated dicarboxylic acids could be used in the presence of N-N'-dicyclohexylcarbodiimide.

KW - Tröger’s base

KW - lactones

KW - amines

KW - cyclization

KW - spiro compounds

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ER -

A New class of tröger's base analogues bearing spiro[4.5] lactone straps

Abstract

Keywords

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