Synthesis of 3,4-Dihydro-2H-1,3-benzoxazines by Condensation of 2-Hydroxyaldehydes and Primary Amines: Application to the Synthesis of Hydroxy-Substituted and Deuterium-Labeled Compounds

Development of a DOPO-containing benzoxazine and its high-performance flame retardant copolybenzoxazines

“…Moreover, in an effort to minimize the generation of oligomers a three-step synthesis, through an imine intermediate which is further reduced with NaBH 4 and made to undergo cyclisation, was recently used [23,24]. This method was also successfully used in the synthesis of aromatic diamine-based benzoxazines, which could not easily be synthesized by the traditional approach [11,12,16,25].…”

Synthesis and Structure–Activity Relationship Studies of 4-((2-Hydroxy-3-methoxybenzyl)amino)benzenesulfonamide Derivatives as Potent and Selective Inhibitors of 12-Lipoxygenase

“…While this route appeared amenable to the facile preparation of numerous synthetic analogues, the standard mild method for reductive aminations utilizing sodium triacetoxyborohydride and catalytic acetic acid afforded little to no product. 23 Instead, a stepwise approach involving preformation of the imine was required with 4-amino- N -(thiazol-2-yl)benzenesulfonamide ( 2 ) and the requisite benzaldehyde overnight in ethanol at reflux. Subsequent reduction of the imine with sodium borohydride provided the desired compounds 1, 8–10 , and 14–33 (Scheme 1, method A).…”

Counterion Effect of Amine Salts on Ring‐Opening Polymerization of 1,3‐Benzoxazines

“…Polybenzoxazines are synthesized by ring‐opening polymerization (ROP) from their corresponding 1,3‐benzoxazine monomers that have six‐membered heterocyclic structure(oxazine ring) containing nitrogen and oxygen atoms ( Scheme ) . The high energy requirement to cleave the oxazine ring makes benzoxazines stable at a wide temperature interval, and depending on the functional groups, some monomers can be durable at ≈ 150 °C or more .…”