We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
[3]-1-Azadendralenes as Versatile Building Blocks for the Stereoselective Synthesis of Polysubstituted Hexahydroquinazolin-2-ones and Hexahydrobenzothiazine-2-imines.
- Authors
Kobayashi, Satoru; Kudo, Kenji; Ito, Ai; Honjo, Takuya; Yata, Masahiro; Otani, Takashi; Kutsumura, Noriki; Saito, Takao; Berrée, Fabienne; Romain, Elise; Tripoteau, Fabien; Carboni, Bertrand
- Abstract
A diene-transmissive hetero-Diels-Alder reaction of cross-conjugated 1-azatrienes (-1-azadendralenes) is described for the synthesis of hexahydroquinazolin-2-ones and hexahydrobenzothiazine-2-imines derivatives. [4+2] Cycloaddition reactions with tosyl isocyanate or aryl isothiocyanates gave mono-cycloadducts with high chemo- and regioselectivities. The second Diels-Alder reaction with representative dienophiles, tetracyanoethylene, N-phenylmaleimide, and methyl vinyl ketone, stereoselectively produced ring-fused nitrogen heterocycles. Skeletal diversity can be accessed by combining the three reaction partners - primary amine, tosyl isocyanate, and cross-conjugated 1-oxatriene - in a different sequential order.
- Subjects
RING formation (Chemistry); STEREOSELECTIVE reaction kinetics; HETEROCYCLIC compounds; CHEMICAL reactions; ORGANIC chemistry research
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 20, p4367
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500474