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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*   Pages 1 - 5 ( 5 )

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.

Affiliation:

Instituto de Tecnologia em Fármacos-Farmanguinhos, Fundação Oswaldo Cruz - Fiocruz, Rio de Janeiro, Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Instituto de Tecnologia em Fármacos-Farmanguinhos, Fundação Oswaldo Cruz - Fiocruz, Rio de Janeiro



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