Transformation reactions of the betti base analog aminonaphthols | Zendy

Szatmári István | Zendy; Hetényi Anasztázia | Zendy; Lázár László | Zendy; Fülöp Ferenc | Zendy

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Transformation reactions of the betti base analog aminonaphthols

Author(s) -

Szatmári István,

Hetényi Anasztázia,

Lázár László,

Fülöp Ferenc

Publication year - 2004

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570410310

Subject(s) - chemistry , salicylaldehyde , ring (chemistry) , acetaldehyde , base (topology) , domino , levulinic acid , aziridine , phosgene , stereochemistry , medicinal chemistry , organic chemistry , ethanol , schiff base , catalysis , mathematical analysis , mathematics

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 ring‐closing abilities of the unsubstituted and phenyl‐substituted aminonaphthols 1 and 2 and of the regioisomeric compounds 1 and 3 .

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