Abstract
A variety of natural and unnatural molecules containing a 5-hydroxyindole moiety have displayed strong pharmacological activities. In this context the Nenitzescu reaction has proven to be extremely useful for the preparation of 5- hydroxyindoles directly from simple and accessible materials like 1,4-benzoquinone and enamines. This review will summarize recent applications for the synthesis of complex 5-hydroxyindole derivatives such as pyrimido[4,5-b]indol-4- amines, 5H-benzo[b]carbazoles, 5-hydroxynaltrindolomorphinans, and 3-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)- 1H-indol-5-yloxy]propylphosphonic acid (LY311727) which possess important biological activities. The Mechanism of the Nenitzescu reaction is discussed and as is recent utilization of solid phase chemistry to the Nenitzescu reaction.
Current Organic Chemistry
Title: Synthetic Applications of the Nenitzescu Reaction to Biologically Active 5-Hydroxyindoles
Volume: 12 Issue: 9
Author(s): Shivaputra A. Patil, Renukadevi Patil and Duane D. Miller
Affiliation:
Abstract: A variety of natural and unnatural molecules containing a 5-hydroxyindole moiety have displayed strong pharmacological activities. In this context the Nenitzescu reaction has proven to be extremely useful for the preparation of 5- hydroxyindoles directly from simple and accessible materials like 1,4-benzoquinone and enamines. This review will summarize recent applications for the synthesis of complex 5-hydroxyindole derivatives such as pyrimido[4,5-b]indol-4- amines, 5H-benzo[b]carbazoles, 5-hydroxynaltrindolomorphinans, and 3-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)- 1H-indol-5-yloxy]propylphosphonic acid (LY311727) which possess important biological activities. The Mechanism of the Nenitzescu reaction is discussed and as is recent utilization of solid phase chemistry to the Nenitzescu reaction.
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Cite this article as:
Patil A. Shivaputra, Patil Renukadevi and Miller D. Duane, Synthetic Applications of the Nenitzescu Reaction to Biologically Active 5-Hydroxyindoles, Current Organic Chemistry 2008; 12 (9) . https://dx.doi.org/10.2174/138527208784567223
DOI https://dx.doi.org/10.2174/138527208784567223 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
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
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