Synthesis of hydrazinoheterocycles from Morita-Baylis-Hillman adducts of nitroalkenes with azodicarboxylates

Organic & Biomolecular Chemistry
Vaijinath ManeIrishi N N Namboothiri

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.

References

Feb 1, 1996·Journal of Natural Products·D C ChauretL Poveda
May 25, 2002·Journal of Natural Products·Chen-Hui ChenYing-Chieh Tsai
Oct 12, 2004·Archives of Pharmacal Research·Hu-Quan YinByung-Hoon Lee
Aug 5, 2005·Biological & Pharmaceutical Bulletin·Marina Pereira De CamposAlexandre Bella Cruz
Mar 10, 2006·Organic Letters·Indubhusan DebIrishi N N Namboothiri
Jun 23, 2006·Organic & Biomolecular Chemistry·Mamta DadwalIrishi N N Namboothiri
Oct 4, 2006·Biological & Pharmaceutical Bulletin·Patrícia Shima LuizeCelso Vataru Nakamura
Oct 13, 2006·Organic & Biomolecular Chemistry·Namrata RastogiIrishi N N Namboothiri
Sep 11, 2007·The Journal of Organic Chemistry·Ferruccio BertoliniMauro Pineschi
Jan 15, 2009·Chemical Reviews·Valérie DeclerckFrédéric Lamaty
Aug 12, 2009·Chemical Communications : Chem Comm·Srivari ChandrasekharBharatam Jagadeesh
Sep 18, 2009·Chemistry : a European Journal·Chun-Li CaoJie Sun
Aug 25, 2010·Organic & Biomolecular Chemistry·Pramod ShanbhagIrishi N N Namboothiri
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Eufrânio N da SilvaAntonio V Pinto
Jun 15, 2011·Organic Letters·Michael A Calter, Na Li
Jun 24, 2011·Nature·Scott A SnyderMaria I Chiriac
Sep 7, 2011·Chemical Society Reviews·Deevi Basavaiah, Gorre Veeraraghavaiah
Dec 4, 2012·Mini Reviews in Medicinal Chemistry·Yubo Jiang, Chunxiang Kuang
Jan 16, 2013·Chemical Communications : Chem Comm·Carlos Jarava-BarreraJosé Alemán
Feb 12, 2013·Chimia·Kirandeep Kaur, Irishi N N Namboothiri
Apr 19, 2013·The Journal of Organic Chemistry·Rahul KumarIrishi N N Nambothiri
Jul 24, 2013·Chemical Communications : Chem Comm·Huajian ZhuHongbin Zou
Jul 26, 2013·Organic & Biomolecular Chemistry·Xiang-Yu ChenSong Ye
Aug 24, 2013·Chimia·Ibai E Valverde, Thomas L Mindt

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