Synthesis and Fungicidal Activity of 1-(Carbamoylmethyl)-2-aryl-3,1-benzoxazines

Abstract

A series of new 1-(carbamoylmethyl)-2-aryl-3,1-benzoxazines were prepared in moderate to good yields by BF3·OEt2-catalyzed reactions of aromatic aldehydes with 2-(N-substituted carbamoylmethylamino)benzyl alcohols. The structures of the target compounds were confirmed by IR, 1H-NMR, 13C-NMR, and elemental analyses. The fungicidal activities of the target compounds against plant fungi were preliminarily evaluated, and some of them exhibited good activity.

Novel Tetrahydroquinazolinamines as Selective Histamine 3 Receptor Antagonists for the Treatment of Obesity

“…The oily crude products thus obtained were purified by column chromatography to give the required arylidenylcyclohexanone derivatives in good to moderate yields (55–68%). These molecules were characterized on the basis of their spectroscopic data and are supported by previous literature. − The appropriately substituted tetrahydroquinazolinamines 4 were accessed by condensation of respective arylidenylcyclohexanones 3 with guanidine hydrochloride in the presence of NaH in dimethylformamide (DMF) as the solvent following earlier reported protocols , (Scheme ). The reaction involves conjugate 1, 4 addition of guanidine to the olefinic bond of the enone followed by cyclization and condensation at the carbonyl end, tautomerization, and aromatization by aerial oxidation, resulting in the formation of the 2-aminopyrimidine nucleus.…”

Formaldehyde-Free Polybenzoxazines for High Performance Thermosets

“…Previous authors used Lewis or Brønsted acids to catalyze the condensation reaction between aldehyde and imine. For instance, Tang et al studied the aza-acetalization of aromatic aldehydes with catalysts such as boron trifluoride, stain tetrachloride, , trimethylsilyl chloride, , and other Lewis or Brønsted acids. They showed in overall that the nucleophilicity of the amine moiety is a key-parameter of this reaction .…”

Synthesis and fungicidal activity of novel ureido-substituted 1,3-benzoxazines

“…The in vitro fungicidal activities of the prepared compounds 6a-d and 7a-j were evaluated adopting the mycelium growth rate test method. 18 The fungicidal activity was tested against Sclerotonia sclerotiorum, Botrytis cinerea, Rhizoctonia solani, Gibberella zeae, Phytophythora capsic and Magnaporthe oryzae at 50 µg mL -1 using chlorothalonil as a reference compound. The activities were expressed as inhibition rate (%) and the results are summarized in Table 2.…”

“…11 The ureido group has high cytokinin activity and selectivity, and a series of bioactive compounds can be formed by integration of a ureido group with 1,5-diarylpyrazoles 12 and with other groups. 13 On the other hand, heterocyclic nitrogen compounds such as 1,3-benzoxazine derivatives have received more and more attention due to their wide range of biological activities including anti-inflammatory, 14 anti-mycobacterial, 15 anti-cancer, 16 anti-fungal 17,18 and anti-plasmodial activity, 19 and as CCR2 and CCR5 dual antagonists, 20 and DNA-PK inhibitors. 21 Molecular hybridization, which involves the combination of two or more distinct bioactive units, is one of the successful strategies for the development of new drug classes.…”

“…21 Molecular hybridization, which involves the combination of two or more distinct bioactive units, is one of the successful strategies for the development of new drug classes. 22,23 Hence, in a continuation of our programs aimed at synthesizing new fungicidal compounds with high fungicidal potency, 17,18 we integrated the ureido group with the 1,3-benzoxazine ring to form novel ureido-substituted 1,3-benzoxazine hybrids. Here we wish to report the preparation and fungicidal activity of the target compounds.…”