Syntheses, Biological and Material Significance of Dihydro[1,3]oxazine Derivatives: An Overview

Abstract

: Dihydro[1,3]oxazines are an important class of heterocyclic compounds having a wide range of biological and material properties. Medicinally, they possess diverse pharmacological activities such as bactericidal, fungicidal, microbiocidal, antitumor, anti-HIV and anti-inflammatory agents. Apart from being biologically active, they are materially useful for making polybenzoxazines. Polybenzoxazines, a novel class of non-conjugated thermosetting materials that belong to the family of addition-curable phenolic resins. They have lucrative properties such as small shrinkage in curing, low water absorption, good thermal stability, no release of volatile materials during cure, no need for catalyst and inexpensive raw materials. Further, the flexibility in designing a monomer gives polybenzoxazines an additional edge over ordinary phenolic resins. This review briefly describes the syntheses including eco-friendly strategies, biological and material significance of various dihydro[1,3]oxazine derivatives.

Progress in the Synthesis of Heterocyclic Compounds Catalyzed by Lipases

“…1,3-Oxazines are one class of the most important heterocyclic compounds, which possess a variety of pharmacological activities, such as bactericidal, antitumor, anti-HIV, anti-inflammatory, etc., and have been widely used in medicine. 47 Zhang et al reported a combined catalytic system using lipase CALB and Ru(bpy) 3 Cl 2 for the reaction of naphthol and ethyl Narylglycinate (instead of ethyl N-alkylglycinate) to produce 1,3-oxazine derivatives (►Scheme 16). 48 The reaction was conducted at r.t. in acetonitrile for 48 hours under a 12 W fluorescent bulb (Philips), and the yield achieved was 19 to 69%.…”

Synthesis and Structural Analysis of Chiral Bis-dihydro[1,3]-naphthoxazines and Imidazolidine Derivatives Prepared by Three-Component Mannich-Type Condensation

“…The synthesis of dihydrooxazines by three-component Mannichtype condensation of naphthol, amine and formaldehyde has a high potential for obtaining an important class of heterocyclic compounds. Structurally diverse dihydro [1,3]oxazines have demonstrated a broad range of biological activities (bactericides, fungicides, antiinflammatory, antitumor, anti-HIV) and have found applications in materials science [3,4].…”

“…The synthesis of dihydro [1,3]oxazines occurs most commonly through one-pot condensation between aromatic alcohol, formaldehyde and amine applying different solvents or in some examples under solvent-free conditions [3]. The use of readily available chiral amines offers the opportunity for synthesis of chiral dihydrooxazines.…”

Antiproliferative Activity of (−)‐Isopulegol‐based 1,3‐Oxazine, 1,3‐Thiazine and 2,4‐Diaminopyrimidine Derivatives

“…On the other hand, 1,3‐thiazine derivatives, an important class of heterocyclic compounds, have a wide range of biological properties[ 66 , 67 ] including antiproliferative,[ 68 , 69 , 70 , 71 , 72 ] analgesic, [73] anticonvulsant,[ 74 , 75 ] anti‐inflammatory, [76] antibiotic, [77] antimicrobial,[ 75 , 78 , 79 , 80 ] antimalarial, [81] and antihypertensive [82] properties. A literature survey revealed that also 1,3‐oxazine moieties exhibit a broad range of pharmacological activities,[ 83 , 84 ] such as anticancer,[ 85 , 86 , 87 , 88 , 89 ] antimicrobial[ 90 , 91 ] and anti‐inflammatory[ 92 , 93 ] effects, which showed their potential value in developing new therapeutic agents.…”