Bicyclic 5-6 Systems with One Bridgehead (Ring Junction) Nitrogen Atom: Three Extra Heteroatoms 3:0

Hajós, György; Riedl, Zsuzsanna

doi:10.1016/b978-008044992-0.01015-4

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2009

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“…This possibility is demonstrated in Scheme 2: if the salt 3 participates in a Dimroth rearrangement, the 3-hydrazino-isoquinoline 6 would be formed, and the treatment of this compound with nitrous acid would afford an azide 5 in equilibrium with the tetrazole 4. 4 In order to clarify the locations of the particular nitrogen atoms in the unsubstituted tetrazole 4a deriving from these atoms in the starting compound 3a, three types of isotope labeling were applied. The two amino-nitrogen atoms of 3a were separately labeled by the 15 Nisotope (i.e.…”

Section: Resultsmentioning

confidence: 99%

A recently recognized ambident reactivity of 2,3-diamino-isoquinolinium salts

Riedl

Filák

Egyed

et al. 2009

Arkivoc

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Reinvestigation of an old experimental finding -the formation of linearly fused tetrazoloisoquinolines from 2,3-diamino-isoquinolinium salts, by using 15 N-labeling and 15 N-NMR spectroscopy, revealed that the ring closure pathway -unlike a recently observed cyclization of the same diamino salt -does not proceed via a rearrangement route. By comparison of this reaction with the entirely different reactivities of other related 1,2-diamino-azinium salts, a general mechanism is suggested, revealing an ambident reactivity of these diamino compounds.

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Section: Resultsmentioning

confidence: 99%