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Formation of pyridazino[4,5-c]pyridazine derivatives upon [4+2]cycloaddition of 4-phenyl-1,2,4-triazoline-3,5-dione to cross-conjugated monoferrocenyltrienes

✍ Scribed by Juan M. Martínezmendoza; Eduardo A. Vázquez López; Rafael Moreno Esparza; Marcos Flores Alamo; Elena I. Klimova

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
178 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Cross‐conjugated monoferrocenyltrienes react with 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione to give mono‐ and bis‐[4+2]‐cycloaddition products. Nonsubstituted and 2,4‐disubstituted 3‐ferrocenylmethylidenepenta‐1,4‐dienes afford respective pyridazine and pyridazino[4,5‐c]pyridazine derivatives. Their structures were established based on ^1^H and ^13^C NMR data and X‐ray diffraction analysis.

📜 SIMILAR VOLUMES

Solvent Effects in [4+2] Cycloadditions
Solvent Effects in [4+2] Cycloadditions of Polyhalogenated Cyclopentadienes with 4-Phenyl-1,2,4-triazoline-3,5-dione
✍ Sauer, Jürgen ;Schuhbauer, Hans Markus 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 497 KB

## Abstract Relative rates of [4 + 2] cycloadditions of cyclopentadienes 1a–1e with 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (2) in 12 different solvents vary by factors of up to 19000, but the reactions show similar solvent effects. Rate constants __k__~2~ correlate well with solvent parameters __AN__

[4+2] Cycloaddition of 2(1H)-pyrazinones
[4+2] Cycloaddition of 2(1H)-pyrazinones and 1,2,4-triazoline-3,5-diones
✍ Takehiko Nishio 📂 Article 📅 1998 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 273 KB

## Abstract The reaction of 2(1__H__)‐pyrazinones 1 and 1,2,4‐triazoline‐3,5‐diones 3 was investigated by comparing that of 1 with singlet oxygen. 2(1__H__)‐Pyrazinones 1 reacted in Diels‐Alder fashion with 1,2,4‐triazoline‐3,5‐diones 3 to afford [4+2]‐adducts 4–17 in high yields.