Journal
TETRAHEDRON LETTERS
Volume 45, Issue 50, Pages 9171-9175Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.10.108
Keywords
isomerization; ring-closing metathesis; benzo-fused heterocycles; 1,4-benzoxazines; 1,6-benzodiazocine; 1,6-berizoxazocine; 1,6-benzothiazocine; 1,5-benzothiazepine
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An isomerization-ring-closing metathesis (RCM) strategy afforded N-substituted 4H-1,4-benzoxazines from the protected N-allyl-2-(allyloxy)anilines. In addition, RCM was used to synthesize the N-substituted, 8-membered benzo-fused heterocycles from the respective diallyl compounds: 1,2,5,6-tetraliydro-1,6-benzodiazocine, 5,6-dihydro-2H-1,6-benzoxazocine, 5,6,9, 10-tetrahydropyrido[2,3-b][1,4]diazocine and 5,6-dihydro-2H-1,6-benzothiazocine 1,1-dioxide. The isomerization-RCM approach also afforded the 7-membered ring system, 2,5-diliydro-1,5-benzothiazepine 1,1-dioxide, from the protected N-allyl-2-(allylsulfonyl)aniline. Furthermore, the structure of 1,6-bis[(4-methylplienyl)sulfonyl]-1,2,5,6-tetrahydro-1,6-benzodiazocine was confirmed by a single crystal X-ray determination. (C) 2004 Elsevier Ltd. All rights reserved.
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