Mane, Vaijinath ; Pandey, Jyoti ; Ayyagari, Narasihmam ; Dey, Chandan ; Kale, Raju ; Namboothiri, Irishi N. N. (2016) Synthesis of hydrazinoheterocycles from Morita–Baylis–Hillman adducts of nitroalkenes with azodicarboxylates Organic and Biomolecular Chemistry, 14 (8). pp. 2427-2438. ISSN 1477-0520
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Official URL: http://doi.org/10.1039/c5ob02656c
Related URL: http://dx.doi.org/10.1039/c5ob02656c
Abstract
Conjugated nitroalkenes and nitrodienes undergo smooth α-hydrazination with azodicarboxylates through an imidazole catalyzed carbon-heteroatom bond formation under Morita-Baylis-Hillman conditions. The resulting hydrazinonitroalkenes take part in 1,3-dipolar cycloaddition with azide under mild conditions to give hydrazinotriazoles. A [3 + 2] annulation with phenols and naphthols involving Michael addition and cyclization as the key steps lead to arenodihydrofurans bearing a key hydrazinodicarboxylate moiety. Both regioisomers of naphthodihydrofurans could be synthesized by our methodology by employing the appropriate naphthol.
Item Type: | Article |
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Source: | Copyright of this article belongs to The Royal Society of Chemistry. |
ID Code: | 121331 |
Deposited On: | 14 Jul 2021 11:17 |
Last Modified: | 14 Jul 2021 11:17 |
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