Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines

Robert G. Giles; Harry  Heaney; M. John Plater

doi:10.1016/j.tet.2015.05.005

Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines

Robert G. Giles, Harry Heaney, M. John Plater

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Abstract

Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basi- fication and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.

Original language	English
Pages (from-to)	7367-7385
Number of pages	19
Journal	Tetrahedron
Volume	71
Issue number	39
Early online date	9 May 2015
DOIs	https://doi.org/10.1016/j.tet.2015.05.005
Publication status	Published - 30 Sep 2015

Keywords

Indole(s)
Pyrrole(s)
Ketones
Secondary amines

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© 2015. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
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Michael Plater
- Chemistry (Research Theme)
- School of Natural & Computing Sciences, Chemistry - Senior Lecturer
Person: Academic

Cite this

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title = "Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines",

abstract = "Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basi- fication and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.",

keywords = "Indole(s), Pyrrole(s), Ketones, Secondary amines",

author = "Giles, {Robert G.} and Harry Heaney and Plater, {M. John}",

note = "I thank SERC for a CASE studentship (to RG. Giles) with the former Fisons Pharmaceuticals division (with Dr. S. C. Eyley) and Dr. B. R. Buckley, of this department, for provided helpful comments on an earlier version of the manuscript.",

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T1 - Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines

AU - Giles, Robert G.

AU - Heaney, Harry

AU - Plater, M. John

N1 - I thank SERC for a CASE studentship (to RG. Giles) with the former Fisons Pharmaceuticals division (with Dr. S. C. Eyley) and Dr. B. R. Buckley, of this department, for provided helpful comments on an earlier version of the manuscript.

PY - 2015/9/30

Y1 - 2015/9/30

N2 - Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basi- fication and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.

AB - Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basi- fication and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.

KW - Indole(s)

KW - Pyrrole(s)

KW - Ketones

KW - Secondary amines

U2 - 10.1016/j.tet.2015.05.005

DO - 10.1016/j.tet.2015.05.005

M3 - Article

VL - 71

SP - 7367

EP - 7385

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 39

ER -

Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines

Abstract

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Michael Plater

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