[:pb]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. [:]

[:pb]Authors: Da Silva, E. T. ; Da Silva, A. A. ; Moraes, A. M. ; De Souza, M. V. N.
Source: Letters in Organic Chemistry, v. 17, p. 165-169, 2020
Publisher: Bentham Science Publishers

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.

Document Type: Letter Paper

DOI: 10.2174/1570178616666190123114922

Publication date: 1 de Março de 2020[:]