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Communication | Regular issue | Vol 60, No. 4, 2003, pp.773-778
Published online, 3rd March, 2003
DOI: 10.3987/COM-02-9697
[2π + 2σ] Type Cycloaddition Reactions of Naphtho[b]cyclopropene with Imine or Carbonyl Derivatives Conjugated with Heteroaromatic Ring to Form Naphtho[b]dihydropyrroles or Furans

Katsuhiro Saito,* Katsuhiko Ono, Masakazu Ohkita, Machiko Fukaya, Kotaro Ono, and Yoji Kondo

*Nagoya Institute of Technology, Department of Applied Chemistry, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Imine derivatives conjugated with heteroaromatic ring such as furan, thiophene or pyrrole reacted with naphtho[b]cyclopropene in the presence of silver or ytterbium catalysts. The reactions proceeded via [2π + 2σ] type cycloaddition process to give naphtho[b]dihydropyrrole derivatives. The yields of the cycloadducts were influenced by the heteroaromatic ring, i.e. the furan derivatives gave high yields and the pyrrole derivatives gave low ones. The effects of the catalysts and the solvents were also investigated. The analogous reactions with heterocyclic aldehydes gave naphtho[b]dihydrofuran derivatives. Furthermore, a reaction with a hydrazone derivative afforded an open chain type adduct.