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Synlett 1999; 1999(10): 1609-1611
DOI: 10.1055/s-1999-2909
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Solid Phase Synthesis of Tricyclic Nitrogen Heterocycles via Intramolecular Diels-Alder Reaction of Furans

K. Paulvannan* , Tao Chen, Jeffrey W. Jacobs
  • *Affymax Research Institute, 3410 Central Expressway, Santa Clara CA 95051, USA; Fax (4 08)4 81-95 58; E-mail: kumar_paulvannan@affymax.com
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Publication Date:
31 December 1999 (online)

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An efficient solid phase synthesis of highly substituted rigid tricyclic nitrogen heterocycles through acylation of resin-bound furylamine with fumaric and maleic acid derivatives has been studied. The product is formed via an initial N-acylation followed by intramolecular Diels-Alder (IMDA) reaction. Impact of electronic and steric effects on the product formation has also been investigated.

intramolecular Diels-Alder reaction - furan - maleic anhydride - solid phase synthesis - tricyclic nitrogen heterocycles