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Synthesis of indazole-N-oxides via the 1,7-electrocyclisation of azomethine ylides

✍ Scribed by Miklós Nyerges; Imre Fejes; Andrea Virányi; Paul W Groundwater; László Tőke

Book ID
104230955
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
93 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first example of the 1,7-electrocyclisation of a non-stabilised azomethine ylide, e.g. 2, onto a nitro group, to give a 1,2,6-oxadiazepine intermediate, e.g. 4, is reported. Subsequent ring contraction results in the formation of the indazole-Noxides 5, 12, and 14.

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1,7-Electrocyclisations of stabilised az
1,7-Electrocyclisations of stabilised azomethine ylides
✍ Miklós Nyerges; Andrea Virányi; Áron Pintér; László Tőke 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 156 KB

Ester-stabilised a,b:g,d-unsaturated azomethine ylides 9 were generated by the deprotonation method from isoquinolinium salts 8. 1,7-Electrocyclisation of these dipoles followed by a 1,5-hydrogen shift, gives tetrahydro [5,6]azepino[2,1a]isoquinolines 10.

1,7-Electrocyclisation of non-stabilised
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✍ Andrea Arany; Paul W. Groundwater; Miklòs Nyerges 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 91 KB

Non-stablilised ct,[B;y,8-unsaturated azomethine ylides 3 were generated by the decarbexylation method from 3,3-diarylpropenals I and secondary amino acids 2. 1,7-Electrocyclisation of these azomethine ylides, followed by a i,5-hydrogen shiit, gives 2,3-dihydru-lH-2-benzazepines 4.