An improved synthesis of hydroxyindoles

Lena Lerman; Marta Weinstock-Rosin; Abraham Nudelman

doi:10.1055/s-2004-834924

An improved synthesis of hydroxyindoles

Lena Lerman, Marta Weinstock-Rosin, Abraham Nudelman

Department of Chemistry

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

19 Scopus citations

Abstract

An improved synthetic procedure for the synthesis of 6- and 7-hydroxyindoles is described. In this method, the addition of two chlorine atoms in 1-benzyloxy-4,5-dichloro-2-nitrobenzene (3) and 1-benzyloxy-2,6- dichloro-3-nitrobenzene (9) facilitated the subsequent cyanomethylation step to give substituted cyanomethyl-dichloronitrobenzenes 4 and 10, leading to an overall increase in the yield of the hydroxyindoles 6 and 12.

Original language	English
Pages (from-to)	3043-3046
Number of pages	4
Journal	Synthesis
Issue number	18
DOIs	https://doi.org/10.1055/s-2004-834924
State	Published - 17 Dec 2004

Bibliographical note

Funding Information:
This study was supported by the ‘Fondo de Investigación Sanitaria-Instituto de Salud Carlos III’ [ PI15/00186 and PI18/00050 to I.I.C., and PI13/01512 , PI16/00201 an PIE15/00065 to F.G.G.]; and the European Regional Development Fund/European Social Fund FIS [FEDER/FSE, Una Manera de Hacer Europa]. MINECO funds support R.R. and O.P. contracts through and RTC-2016-5314-1 project. The funding sources did not provide any input in the development of the research and manuscript.

Funding Information:
This study was supported by the ?Fondo de Investigaci?n Sanitaria-Instituto de Salud Carlos III? [PI15/00186 and PI18/00050 to I.I.C., and PI13/01512, PI16/00201 an PIE15/00065 to F.G.G.]; and the European Regional Development Fund/European Social Fund FIS [FEDER/FSE, Una Manera de Hacer Europa]. MINECO funds support R.R. and O.P. contracts through and RTC-2016-5314-1 project. The funding sources did not provide any input in the development of the research and manuscript.

Funding

This study was supported by the ‘Fondo de Investigación Sanitaria-Instituto de Salud Carlos III’ [ PI15/00186 and PI18/00050 to I.I.C., and PI13/01512 , PI16/00201 an PIE15/00065 to F.G.G.]; and the European Regional Development Fund/European Social Fund FIS [FEDER/FSE, Una Manera de Hacer Europa]. MINECO funds support R.R. and O.P. contracts through and RTC-2016-5314-1 project. The funding sources did not provide any input in the development of the research and manuscript. This study was supported by the ?Fondo de Investigaci?n Sanitaria-Instituto de Salud Carlos III? [PI15/00186 and PI18/00050 to I.I.C., and PI13/01512, PI16/00201 an PIE15/00065 to F.G.G.]; and the European Regional Development Fund/European Social Fund FIS [FEDER/FSE, Una Manera de Hacer Europa]. MINECO funds support R.R. and O.P. contracts through and RTC-2016-5314-1 project. The funding sources did not provide any input in the development of the research and manuscript.

Funders	Funder number
de Salud Carlos III
Ministerio de EconomÃa y Competitividad	RTC-2016-5314-1
Instituto de Salud Carlos III	PI18/00050, PI15/00186, PI13/01512, PI16/00201, PIE15/00065
European Regional Development Fund

Keywords

Cyanomethylation
Hydroxyindoles
Indole synthesis

Access to Document

10.1055/s-2004-834924

Cite this

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title = "An improved synthesis of hydroxyindoles",

abstract = "An improved synthetic procedure for the synthesis of 6- and 7-hydroxyindoles is described. In this method, the addition of two chlorine atoms in 1-benzyloxy-4,5-dichloro-2-nitrobenzene (3) and 1-benzyloxy-2,6- dichloro-3-nitrobenzene (9) facilitated the subsequent cyanomethylation step to give substituted cyanomethyl-dichloronitrobenzenes 4 and 10, leading to an overall increase in the yield of the hydroxyindoles 6 and 12.",

keywords = "Cyanomethylation, Hydroxyindoles, Indole synthesis",

author = "Lena Lerman and Marta Weinstock-Rosin and Abraham Nudelman",

note = "Funding Information: This study was supported by the {\textquoteleft}Fondo de Investigaci{\'o}n Sanitaria-Instituto de Salud Carlos III{\textquoteright} [ PI15/00186 and PI18/00050 to I.I.C., and PI13/01512 , PI16/00201 an PIE15/00065 to F.G.G.]; and the European Regional Development Fund/European Social Fund FIS [FEDER/FSE, Una Manera de Hacer Europa]. MINECO funds support R.R. and O.P. contracts through and RTC-2016-5314-1 project. The funding sources did not provide any input in the development of the research and manuscript. Funding Information: This study was supported by the ?Fondo de Investigaci?n Sanitaria-Instituto de Salud Carlos III? [PI15/00186 and PI18/00050 to I.I.C., and PI13/01512, PI16/00201 an PIE15/00065 to F.G.G.]; and the European Regional Development Fund/European Social Fund FIS [FEDER/FSE, Una Manera de Hacer Europa]. MINECO funds support R.R. and O.P. contracts through and RTC-2016-5314-1 project. The funding sources did not provide any input in the development of the research and manuscript.",

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N2 - An improved synthetic procedure for the synthesis of 6- and 7-hydroxyindoles is described. In this method, the addition of two chlorine atoms in 1-benzyloxy-4,5-dichloro-2-nitrobenzene (3) and 1-benzyloxy-2,6- dichloro-3-nitrobenzene (9) facilitated the subsequent cyanomethylation step to give substituted cyanomethyl-dichloronitrobenzenes 4 and 10, leading to an overall increase in the yield of the hydroxyindoles 6 and 12.

AB - An improved synthetic procedure for the synthesis of 6- and 7-hydroxyindoles is described. In this method, the addition of two chlorine atoms in 1-benzyloxy-4,5-dichloro-2-nitrobenzene (3) and 1-benzyloxy-2,6- dichloro-3-nitrobenzene (9) facilitated the subsequent cyanomethylation step to give substituted cyanomethyl-dichloronitrobenzenes 4 and 10, leading to an overall increase in the yield of the hydroxyindoles 6 and 12.

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An improved synthesis of hydroxyindoles

Abstract

Bibliographical note

Funding

Keywords

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