A Mild and Efficient Synthesis of Novel Isoxazolyl‐Benzo[d]Pyrazino[2, 1‐b] [1, 3]Oxazoles. (11th June 2014)

• Record Type: Journal Article
• Authors: Rajanarendar, Eligeti; Venkateshwarlu, Paka; Ramakrishna, Saini; Nagaraju, Dharavath
• Is Part Of: Journal of heterocyclic chemistry. Volume 52:Number 4(2015)
• Page Start: 1007
• Page End: 1013
• Publication Date: 2014-06-11
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2064
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Synthesis of novel 2‐3‐methyl‐5‐[(<italic>E</italic>)‐2‐aryl‐1‐ethenyl]‐4‐isoxazolyl‐4, 10a‐diaryl‐1, 10a‐dihydro‐2<italic>H</italic>‐benzo[<italic>d</italic>]pyrazino[2, 1‐<italic>b</italic>][1, 3]oxazoles <bold>5</bold> were simply achieved by the reaction of 2‐[3‐methyl‐5‐[(<italic>E</italic>)‐2‐aryl‐1‐ethenyl]‐4‐isoxazolyl(2‐oxo‐2‐arylethyl)amino]‐1‐aryl‐1‐ethanones <bold>3</bold> with <italic>o</italic>‐aminophenol <bold>4</bold> in the presence of CAN catalyst. The intermediates, 2‐[3‐methyl‐5‐[(<italic>E</italic>)‐2‐aryl‐1‐ethenyl]‐4‐isoxazolyl(2‐oxo‐2‐arylethyl)amino]‐1‐aryl‐1‐ethanones <bold>3</bold>, were prepared by the reaction of 4‐amino‐3‐methyl‐5‐styrylisoxazole <bold>1</bold>, with phenacylbromides <bold>2</bold> in ethanol in the presence of K₂CO₃. The structures of the newly synthesized compounds <bold>3a</bold>, <bold>3b</bold>, <bold>3c</bold>, <bold>3d</bold>, <bold>3e</bold>, <bold>3f</bold>, <bold>3g</bold>, <bold>3h</bold>, <bold>3i</bold>, <bold>3j</bold>, <bold>3k</bold>, <bold>3l</bold> and <bold>5a</bold>, <bold>5b</bold>, <bold>5c</bold>, <bold>5d</bold>, <bold>5e</bold>, <bold>5f</bold>, <bold>5g</bold>, <bold>5h</bold>, <bold>5i</bold>, <bold>5j</bold>, <bold>5k</bold>, <bold>5l</bold> have been confirmed by analytical and spectral data.</p> </abstract>