Abstract
Background: Substituted 2-nitroanilines are synthetic intermediates used in the synthesis of important bioactive compounds. Nucleophilic aromatic substitution reactions with activated substrates, such as substituted 5-chloro-2-nitroanilines, usually involve the use of a solvent, high pressure conditions and prolonged reaction times. We describe a simple and straightforward protocol to prepare 5-substituted 2-nitroanilines that addresses these drawbacks.
Methods: Utilizing microwave irradiation and solvent free conditions, a series of 5-alkylamino-2- nitroanilines (1-14) have been efficiently prepared by reacting 4,5-dichloro-2-nitroaniline with different primary and cyclic secondary amines.
Results: The reactions proceeded in short periods of time (5-35 min) without side products, facilitating the isolation of 1- 14 in 55-93% yields. Reactions under microwave conditions were faster than those achieved with conventional heating.
Conclusion: This simplified approach can be a suitable alternative to synthetic methods involving conventional heating. The reported methodology can be applied to generate a variety of 5-substituted 2-nitroanilines which serve as precursors to compounds of pharmaceutical interest.
Keywords: 5-Substituted 2-nitroaniline, amine, green chemistry, microwave-assisted synthesis, nucleophilic aromatic substitution, solvent-free synthesis.
Call for Papers in Thematic Issues
Microwave Technology: Advancements and Applications in Chemistry, Environment and Food Science
Microwave technology has emerged as a transformative tool in various fields, offering unique opportunities for rapid, efficient, and clean processes. This thematic issue aims to encapsulate the latest research, innovative strategies, and progressive methodologies concerning the application of microwave technology in three main areas: Chemistry: Highlighting the advancements in microwave-assisted ...read more
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