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Note | Regular issue | Vol 53, No. 4, 2000, pp.917-927
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8811
Nitrilimine Cycloadditions onto Partially Saturated Furo[3,4-c]thieno[2,3-d]pyrazoles. A Problem in Site Selectivity

Gianluigi Broggini, Luisa Garanti,* Giorgio Molteni, and Gaetano Zecchi

*Dipartimento di Chimica Organica e Industriale dell’Università and Centro CNR, Via Golgi 19, 20133 Milano, Italy


Partially saturated furo[3,4-c]thieno[2,3-d]pyrazoles (7-10) have been submitted to 1,3-dipolar cycloaddition with a variety of nitrilimines. The competitive formation of products due to the dipolar attack at different dipolarophilic sites has been observed. The experimental evidence is discussed by taking into account electronic features of the reactive species as well as their steric encumbrance.