Condensation of N-(2-hydroxybenzylidene)-1,2-aminoalkanols with formaldehyde

By means of simple or domino ring-closure reactions of 1-(α-aminobenzyl)-2-naphthol (Betti base: 1), 1-aminomethyl-2-naphthol (2) and 2-(α-aminobenzyl)-1-naphthol (reverse Betti base: 3) with phosgene, ethyl benzimidate, 2-carboxybenzaldehyde, levulinic acid, salicylaldehyde/formalin or salicylaldehyde/acetaldehyde, naphth[1,2-e][1,3]oxazine and naphth[2,1-e][1,3]oxazine derivatives were prepared. All of the nitrogen-bridged polycyclic derivatives of 1 and 3 containing a number of centers of asymmetry were formed with nearly complete diastereoselectivity. Considerable differences were observed in the ringclosing abilities of the unsubstituted and phenyl-substituted aminonaphthols 1 and 2 and of the regioisomeric compounds 1 and 3.

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Transformation reactions of the betti base analog aminonaphthols

Szatmári

Hetényi

Lázár

et al. 2004

Journal of Heterocyclic Chem

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Synthesis of some new N,N′-diarylsubstituted methylene-bis-dihydro-2H-1,3-benzoxazines

Reddy

Raghu

2008

Chinese Chemical Letters

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ADACHI¹

2003

Journal of The Surface Finishing Society of Japan

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Condensation of N-(2-hydroxybenzylidene)-1,2-aminoalkanols with formaldehyde

Cited by 3 publications

References 2 publications

Transformation reactions of the betti base analog aminonaphthols

Transformation reactions of the betti base analog aminonaphthols

Synthesis of some new N,N′-diarylsubstituted methylene-bis-dihydro-2H-1,3-benzoxazines

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