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

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.

Synthesis of Acrylic Acid Derivatives: A Fast, Multigram Scale Methodology via Ultrasound Irradiation / Obtenção de Derivados de Ácidos Acrílicos: Uma Metodologia Rápida, em Escala Multigrama, por Irradiação de Ultrassom

“…However, the application of ultrasound to multigram and large scale preparations remains limited [15] . Lately, we have been focusing our efforts on the development of novel, easy synthetic procedures for the obtainment of high added-value building blocks in multigram and pre-pilot scale using sonochemistry [16,17] . In this context, we have synthesized 3-(2thienyl)acrylic acid and a few cinnamic acid derivatives in multigram scale under ultrasound irradiation.…”