Transformation reactions of the Betti base analog aminonaphthols

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Abstract

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 salicyl-aldehyde/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.

Original languageEnglish
Pages (from-to)367-373
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume41
Issue number3
Publication statusPublished - May 2004

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Oxazines
Phosgene
Derivatives
Acetaldehyde
Aldehydes
Formaldehyde
Nitrogen
2-naphthol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Transformation reactions of the Betti base analog aminonaphthols",
abstract = "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 salicyl-aldehyde/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.",
author = "I. Szatm{\'a}ri and A. Het{\'e}nyi and L. L{\'a}z{\'a}r and F. F{\"u}l{\"o}p",
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TY - JOUR

T1 - Transformation reactions of the Betti base analog aminonaphthols

AU - Szatmári, I.

AU - Hetényi, A.

AU - Lázár, L.

AU - Fülöp, F.

PY - 2004/5

Y1 - 2004/5

N2 - 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 salicyl-aldehyde/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.

AB - 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 salicyl-aldehyde/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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