title: Synthesis of hydrazinoheterocycles from Morita-Baylis-Hillman adducts of nitroalkenes with azodicarboxylates.
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.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India. irishi@iitb.ac.in.
authors.forename: Vaijinath
authors.initials: V
authors.lastname: Mane
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India. irishi@iitb.ac.in.
authors.forename: Jyoti
authors.initials: J
authors.lastname: Pandey
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India. irishi@iitb.ac.in.
authors.forename: Narasihmam
authors.initials: N
authors.lastname: Ayyagari
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India. irishi@iitb.ac.in.
authors.forename: Chandan
authors.initials: C
authors.lastname: Dey
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India. irishi@iitb.ac.in.
authors.forename: Raju
authors.initials: R
authors.lastname: Kale
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India. irishi@iitb.ac.in.
authors.forename: Irishi N N
authors.initials: IN
authors.lastname: Namboothiri