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Synthesis 2000; 2000(10): 1449-1453
DOI: 10.1055/s-2000-7108
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Synthesis of Conformationally Constrained Spirohydantoins with a Dibenzo[a,d]heptadiene Ring

Bin Tao* , Jack W. Timberlake
  • *Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA; Fax + 1(504)2 80 68 60; E-mail: jtimberl@uno.edu
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Publication History

Publication Date:
31 December 2000 (online)

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Conformationally constrained dibenzo[a,d]cycloheptadiene-based spirohydantoins were prepared from dibenzosuberone via the transformation of the α-hydroxy ester to the azido ester, followed by its reduction to the amino ester, and cyclization of the carbomethoxy N,N′-asymmetric ureas, derived from the amino ester with triphosgene and a variety of amines. A novel ring expansion reaction was also observed in the process.

spirohydantoins - triphosgene - N,N′-asymmetric ureas - 6-carbomethoxy-11,12-dihydrodibenz[b,f]azocine - ring expansion reaction

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