Aqueous N-Heterocyclization of Primary Amines and Hydrazines with Dihalides:  Microwave-Assisted Syntheses of N-Azacycloalkanes, Isoindole, Pyrazole, Pyrazolidine, and Phthalazine Derivatives

The synthesis of nitrogen-containing heterocycles from alkyl dihalides (ditosylates) and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. This improved greener synthetic methodology provides...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-01, Vol.71 (1), p.135-141
Main Authors: Ju, Yuhong, Varma, Rajender S
Format: Article
Language:English
Subjects:
Alkanes - chemical synthesis
Alkanes - chemistry
Alkylation
Amines - chemistry
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Hot Temperature
Hydrazines - chemistry
Hydrogen - chemistry
Indoles - chemistry
Isomerism
Microwaves
Molecular Structure
Molecular Weight
Nitrogen - chemistry
Organic chemistry
Phthalazines - chemistry
Preparations and properties
Pyrazoles - chemistry
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Description
Summary:The synthesis of nitrogen-containing heterocycles from alkyl dihalides (ditosylates) and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. This improved greener synthetic methodology provides a simple and straightforward one-pot approach to the synthesis of a variety of heterocycles, such as substituted azetidines, pyrrolidines, piperidines, azepanes, N-substituted 2,3-dihydro-1H-isoindoles, 4,5-dihydropyrazoles, pyrazolidines, and 1,2-dihydrophthalazines.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051878h