Products from heterodiene synthesis and 1,3-cycloaddition in the reaction of N,N-disubstituted 2-aminooxazoles with maleimide

Selected Methodologies Convenient for the Synthesis of N,5‐Diaryloxazole‐2‐amine Pharmacophore

“…1). Compounds containing N,5-diaryloxazole-2-amine moiety are mostly antineoplastic species targeting the following: VEGF receptors (264 molecules) [3], inosine monophosphate dehydrogenase II (242) [4], epidermal growth factor receptors (228) [5], cyclin-dependent kinases 2 and 4 (225) [5], platelet-derived growth factor receptors (225) [5], capsaicin receptors (87) [6], protein tyrosine phosphatase 1B (55) [7], blood-coagulation factor VIIa (50) [8], diacylglycerol acyltransferase (41) [9], cKit tyrosine kinase (19) [10], Flt1 and Flt3 receptor kinases (18) [11], BCR-ABL kinase (18) [9], tubulins (16) [12], and fibroblast growth factor receptors (7) [13]. Derivatives of N,5-diaryloxazole-2-amine 1 are described as anti-angiogenic and antitumor agents [3,4], antibiotics [8], immunosuppressants [8], anti-inflammatory compounds [8], antiviral compounds [4], fungicides [4], platelet aggregation inhibitors [4], antirheumatics [10], antidiabetics [7], anti-obesity agents [8], anti-arteriosclerotics [10], and allergy inhibitors [9].…”

“…"The urea methodology": a reaction of urea (7) or its derivatives VIII with α-halocarbonyls IX. The reaction of urea (7) or its derivatives VIII with α-bromo (or α-chloro) ketones or aldehydes IX represents a useful methodology for the synthesis of oxazole-2-amines X (Scheme 3) [18]. Syntheses of oxazole-2-amines X from urea (7) [19,20] or Scheme 2.…”