Synthesis and nitrogen elimination of the linearly fused tetrazolo (1,5-b) isoquinolinium salts. Formation of a new tetracycle: Indazolo (2,3-b) isoquinoline

A. Messmer, G. Hajós, A. Gelléri, L. Radics

Research output: Contribution to journalArticle

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Abstract

Treatment of 3-aminoisoquinoline (1) with aryldi-azonium salts gave 2-amino-4-arylazoisoquinolines (2) which reacted with aromatic aldehyde to yield imidazo(4,5-c) iso-quinolines. With 3-amino-4-methylisoquinoline (4), however, the same reaction led to 3-isoquinolyltriazenes (5), and these could then be cyclized by the use of "TBB" to give tetrazolo(1,5-b)-isoquinolinium salts (6). The latter azolium salt (6) showed ambident reactivity in the presence of hydroxide ion manifested by simultaneous formation of tolualdehyde derivative 10 and indazolo (3,2-b) isoquinoline system (8). This ambidency as well as the difference in behaviour between the new linearly fused system (6) and its formerly studied angularly fused isomers ("annelation effect") is interpreted in terms of the frontier molecular orbital theory.

Original languageEnglish
Pages (from-to)5415-5426
Number of pages12
JournalTetrahedron
Volume42
Issue number19
DOIs
Publication statusPublished - 1986

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Nitrogen
Salts
Quinolines
Molecular orbitals
Aldehydes
Isomers
Derivatives
isoquinoline
hydroxide ion
1-aminoisoquinoline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and nitrogen elimination of the linearly fused tetrazolo (1,5-b) isoquinolinium salts. Formation of a new tetracycle : Indazolo (2,3-b) isoquinoline. / Messmer, A.; Hajós, G.; Gelléri, A.; Radics, L.

In: Tetrahedron, Vol. 42, No. 19, 1986, p. 5415-5426.

Research output: Contribution to journalArticle

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abstract = "Treatment of 3-aminoisoquinoline (1) with aryldi-azonium salts gave 2-amino-4-arylazoisoquinolines (2) which reacted with aromatic aldehyde to yield imidazo(4,5-c) iso-quinolines. With 3-amino-4-methylisoquinoline (4), however, the same reaction led to 3-isoquinolyltriazenes (5), and these could then be cyclized by the use of {"}TBB{"} to give tetrazolo(1,5-b)-isoquinolinium salts (6). The latter azolium salt (6) showed ambident reactivity in the presence of hydroxide ion manifested by simultaneous formation of tolualdehyde derivative 10 and indazolo (3,2-b) isoquinoline system (8). This ambidency as well as the difference in behaviour between the new linearly fused system (6) and its formerly studied angularly fused isomers ({"}annelation effect{"}) is interpreted in terms of the frontier molecular orbital theory.",
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AU - Hajós, G.

AU - Gelléri, A.

AU - Radics, L.

PY - 1986

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N2 - Treatment of 3-aminoisoquinoline (1) with aryldi-azonium salts gave 2-amino-4-arylazoisoquinolines (2) which reacted with aromatic aldehyde to yield imidazo(4,5-c) iso-quinolines. With 3-amino-4-methylisoquinoline (4), however, the same reaction led to 3-isoquinolyltriazenes (5), and these could then be cyclized by the use of "TBB" to give tetrazolo(1,5-b)-isoquinolinium salts (6). The latter azolium salt (6) showed ambident reactivity in the presence of hydroxide ion manifested by simultaneous formation of tolualdehyde derivative 10 and indazolo (3,2-b) isoquinoline system (8). This ambidency as well as the difference in behaviour between the new linearly fused system (6) and its formerly studied angularly fused isomers ("annelation effect") is interpreted in terms of the frontier molecular orbital theory.

AB - Treatment of 3-aminoisoquinoline (1) with aryldi-azonium salts gave 2-amino-4-arylazoisoquinolines (2) which reacted with aromatic aldehyde to yield imidazo(4,5-c) iso-quinolines. With 3-amino-4-methylisoquinoline (4), however, the same reaction led to 3-isoquinolyltriazenes (5), and these could then be cyclized by the use of "TBB" to give tetrazolo(1,5-b)-isoquinolinium salts (6). The latter azolium salt (6) showed ambident reactivity in the presence of hydroxide ion manifested by simultaneous formation of tolualdehyde derivative 10 and indazolo (3,2-b) isoquinoline system (8). This ambidency as well as the difference in behaviour between the new linearly fused system (6) and its formerly studied angularly fused isomers ("annelation effect") is interpreted in terms of the frontier molecular orbital theory.

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