Abstract
Single enantiomers of functionalised benzopyran-3-amines are widely used in the pharmaceutical industry as building blocks or intermediates in the synthesis of drugs acting as 5-hydroxytryptamine and dopamine receptor ligands, as well as inhibitors of dopamine β-monooxygenase. Several approaches for the preparation of the key benzopyran-3-amine intermediates in optically pure form are discussed, including synthesis and resolution of racemic mixtures, application of starting materials from the chiral pool, asymmetric synthesis and chromatographic techniques. Several examples of some larger scale production processes are provided, together with a discussion of the advantages and limitations of each approach.
Current Organic Chemistry
Title: Approaches to Enantiomerically Pure 3,4-Dihydro-2H-1-Benzopyran-3-Amines
Volume: 14 Issue: 6
Author(s): A. Beliaev, B. Broadbelt and D. A. Learmonth
Affiliation:
Abstract: Single enantiomers of functionalised benzopyran-3-amines are widely used in the pharmaceutical industry as building blocks or intermediates in the synthesis of drugs acting as 5-hydroxytryptamine and dopamine receptor ligands, as well as inhibitors of dopamine β-monooxygenase. Several approaches for the preparation of the key benzopyran-3-amine intermediates in optically pure form are discussed, including synthesis and resolution of racemic mixtures, application of starting materials from the chiral pool, asymmetric synthesis and chromatographic techniques. Several examples of some larger scale production processes are provided, together with a discussion of the advantages and limitations of each approach.
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Cite this article as:
Beliaev A., Broadbelt B. and Learmonth A. D., Approaches to Enantiomerically Pure 3,4-Dihydro-2H-1-Benzopyran-3-Amines, Current Organic Chemistry 2010; 14 (6) . https://dx.doi.org/10.2174/138527210790820249
DOI https://dx.doi.org/10.2174/138527210790820249 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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