A Dieckmann cyclization route to piperazine-2,5-diones | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7416396

Reference Type

Journal Article

Title

A Dieckmann cyclization route to piperazine-2,5-diones

Author(s)

Aboussafy, CL; Clive, DL; ,

Year

2012

Is Peer Reviewed?

Yes

Journal

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904

Publisher

AMER CHEMICAL SOC

Location

WASHINGTON

Volume

Issue

Page Numbers

5125-5131

Language

English

PMID

22563847

DOI

10.1021/jo3007144

Web of Science Id

WOS:000304682400026

URL

https://pubs.acs.org/doi/10.1021/jo3007144
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Abstract

Piperazine-2,5-diones are formed by Dieckmann cyclization (NaH, THF) of substructures of the type CH(2)-N(R)C(O)CH(2)N(R')CO(2)Ph in which the terminal methylene (CH(2)) that is adjacent to nitrogen closes onto the carbonyl group of the phenyl carbamate unit at the other end of the chain. R and R' are alkyl groups, and the terminal methylene is activated by a ketone carbonyl, a nitrile, an ester, or a phosphoryl group. The starting materials are assembled by standard acylation and oxidation processes, starting from a β-(alkylamino)alcohol, an (alkylamino)acetonitrile, an (alkylamino) ester, or an (alkylamino)methyl phosphonate.

Keywords

Alkyl groups; Carbonyl groups; Dieckmann cyclization; Oxidation process; Phosphonates; Phosphoryl groups; Acetonitrile; Carbon dioxide; Cyanides; Esterification; Esters; Ketones; Cyclization; 2,5 piperazinedione derivative; acetonitrile; alcohol; carbamic acid; carbene; ester; ketone; methylphosphonic acid; nitrogen; piperazine derivative; sodium hydroxide; unclassified drug; acylation; article; chemical structure; cyclization; Dieckmann reaction; oxidation; synthesis; Crystallography, X-Ray; Cyclization; Magnetic Resonance Spectroscopy; Models, Molecular; Nitriles; Organophosphonates; Piperazines