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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

Multigram-scale Synthesis of Building Block Nitro-imine Derivative by Using Classical Method and Ultrasound Irradiation and Conversion to Imino-alcohol Derivative, Using Camphor as Starting Material

Author(s): Emerson Teixeira da Silva, Adriele da Silva Araújo, Adriana Marques Moraes and Marcus Vinícius Nora de Souza*

Volume 17, Issue 3, 2020

Page: [165 - 169] Pages: 5

DOI: 10.2174/1570178616666190123114922

Price: $65

Abstract

This study describes a simple multigram-scale procedure for the preparation of (E)-N-(1,7,7- trimethylbicyclo[2.2.1]heptan-2-ylidene)nitramide, nitro-imine 2, by using both classical methods and ultrasound irradiation from 1 utilizing Camphor, a natural product, as starting material. This key intermediate 2, a good building block, is useful to prepare various substances such as terpenoids, reagents for large-scale hydroxylation and amination of organic substrates, and derivatives with anticonvulsant, hypoglycemic, anti-inflammatory, antimicrobial and antiviral activities. It can be transformed into a wide range of other derivatives which can then also be employed in inorganic chemistry. In this work, another useful derivative (E)-2-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)ethanol 3 has been prepared from nitro-imine 2 on multigram-scale which also allows access to a variety of products of biological interest after suitable chemical transformations.

Keywords: Camphor, Multigram-scale synthesis, Ultrasound, Oxime, Nitro-imine, Building Block, structure-activity.

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