An Efficient Synthesis of Novel Benzo‐Fused Macrocyclic Dilactams. Issue 7 (12th July 2013)

• Record Type: Journal Article
• Authors: Mekky, Ahmed E. M.; Ahmed, Ahmed A. M.; Elwahy, Ahmed H. M.
• Is Part Of: Helvetica chimica acta. Volume 96:Issue 7(2013:Jul.)
• Page Start: 1290
• Page End: 1297
• Publication Date: 2013-07-12
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201200529
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A facile synthetic approach was adopted towards the synthesis of benzo‐fused macrocyclic lactams <bold>2a</bold>–<bold>2g</bold><italic>via</italic> the base‐catalyzed condensation reaction of 2, 2′‐[alkanediylbis(oxy)]bis[benzaldehydes] <bold>3a</bold>–<bold>3c</bold> with <italic>N</italic>, <italic>N′</italic>‐substituted bis[2‐cyanoacetamide] derivatives <bold>7a</bold>–<bold>7c</bold> (<italic>Scheme 2</italic>). The latter compounds were obtained by the reaction of the appropriate diamines <bold>6a</bold>–<bold>6c</bold> with ethyl 2‐cyanoacetate (<bold>4</bold>). Attempts to prepare the oxaaza macrocycles <bold>2</bold> by alternative pathways were also investigated. The novel pyrazolo‐fused macrocycles <bold>13a</bold> and <bold>13b</bold> were obtained in 48 and 52% yield, respectively, upon treatment of <bold>2d</bold> and <bold>2g</bold> with NH₂NH₂⋅H₂O at 100° (<italic>Scheme 4</italic>).</p> </abstract>