Synthesis and structural study of azidonaphtho-as-triazines

"Annelation effect" in azide-tetrazole equlibria

G. Hajós, A. Messmer, A. Neszmélyi, L. Párkányí

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Azide derivatives of the three possible (two angular and one linear) naphtho-as-triazines 7a, 10a, and 15a were prepared and the equilibria leading to fused tetrazoles were investigated by NMR spectroscopy and X-ray analysis. Comparison of the differently annelated systems (topological isomere) revealed an essential "annelation effect": while 3-azidonaphtho[2,1-c]-as-triazine (7a) and 3-azidonaphtho[1,2-c]-as-triazine (10a) formed "b-fused" tetrazoles 7b and 10b, the linear 3-azidonaphtho[2,3-e]-as-triazine (15a) resulted in the "c-fused" tetrazole compound 15c. For the differences between behavior of the angular and the linear azidonaphthotriazines, a possible interpretation is presented by extension of Clar's principle to heteroaromatic systems.

Original languageEnglish
Pages (from-to)3199-3203
Number of pages5
JournalJournal of Organic Chemistry
Volume49
Issue number17
Publication statusPublished - 1984

Fingerprint

Triazines
Azides
Tetrazoles
X ray analysis
Nuclear magnetic resonance spectroscopy
Derivatives
1H-tetrazole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and structural study of azidonaphtho-as-triazines : "Annelation effect" in azide-tetrazole equlibria. / Hajós, G.; Messmer, A.; Neszmélyi, A.; Párkányí, L.

In: Journal of Organic Chemistry, Vol. 49, No. 17, 1984, p. 3199-3203.

Research output: Contribution to journalArticle

@article{7726657507bf4d62a81fb45a2b4be5c7,
title = "Synthesis and structural study of azidonaphtho-as-triazines: {"}Annelation effect{"} in azide-tetrazole equlibria",
abstract = "Azide derivatives of the three possible (two angular and one linear) naphtho-as-triazines 7a, 10a, and 15a were prepared and the equilibria leading to fused tetrazoles were investigated by NMR spectroscopy and X-ray analysis. Comparison of the differently annelated systems (topological isomere) revealed an essential {"}annelation effect{"}: while 3-azidonaphtho[2,1-c]-as-triazine (7a) and 3-azidonaphtho[1,2-c]-as-triazine (10a) formed {"}b-fused{"} tetrazoles 7b and 10b, the linear 3-azidonaphtho[2,3-e]-as-triazine (15a) resulted in the {"}c-fused{"} tetrazole compound 15c. For the differences between behavior of the angular and the linear azidonaphthotriazines, a possible interpretation is presented by extension of Clar's principle to heteroaromatic systems.",
author = "G. Haj{\'o}s and A. Messmer and A. Neszm{\'e}lyi and L. P{\'a}rk{\'a}ny{\'i}",
year = "1984",
language = "English",
volume = "49",
pages = "3199--3203",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Synthesis and structural study of azidonaphtho-as-triazines

T2 - "Annelation effect" in azide-tetrazole equlibria

AU - Hajós, G.

AU - Messmer, A.

AU - Neszmélyi, A.

AU - Párkányí, L.

PY - 1984

Y1 - 1984

N2 - Azide derivatives of the three possible (two angular and one linear) naphtho-as-triazines 7a, 10a, and 15a were prepared and the equilibria leading to fused tetrazoles were investigated by NMR spectroscopy and X-ray analysis. Comparison of the differently annelated systems (topological isomere) revealed an essential "annelation effect": while 3-azidonaphtho[2,1-c]-as-triazine (7a) and 3-azidonaphtho[1,2-c]-as-triazine (10a) formed "b-fused" tetrazoles 7b and 10b, the linear 3-azidonaphtho[2,3-e]-as-triazine (15a) resulted in the "c-fused" tetrazole compound 15c. For the differences between behavior of the angular and the linear azidonaphthotriazines, a possible interpretation is presented by extension of Clar's principle to heteroaromatic systems.

AB - Azide derivatives of the three possible (two angular and one linear) naphtho-as-triazines 7a, 10a, and 15a were prepared and the equilibria leading to fused tetrazoles were investigated by NMR spectroscopy and X-ray analysis. Comparison of the differently annelated systems (topological isomere) revealed an essential "annelation effect": while 3-azidonaphtho[2,1-c]-as-triazine (7a) and 3-azidonaphtho[1,2-c]-as-triazine (10a) formed "b-fused" tetrazoles 7b and 10b, the linear 3-azidonaphtho[2,3-e]-as-triazine (15a) resulted in the "c-fused" tetrazole compound 15c. For the differences between behavior of the angular and the linear azidonaphthotriazines, a possible interpretation is presented by extension of Clar's principle to heteroaromatic systems.

UR - http://www.scopus.com/inward/record.url?scp=33845471023&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33845471023&partnerID=8YFLogxK

M3 - Article

VL - 49

SP - 3199

EP - 3203

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 17

ER -