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[3]‐1‐Azadendralenes as Versatile Building Blocks for the Stereoselective Synthesis of Polysubstituted Hexahydroquinazolin‐2‐ones and Hexahydrobenzothiazine‐2‐imines
Author(s) -
Kobayashi Satoru,
Kudo Kenji,
Ito Ai,
Honjo Takuya,
Yata Masahiro,
Otani Takashi,
Kutsumura Noriki,
Saito Takao,
Berrée Fabienne,
Romain Elise,
Tripoteau Fabien,
Carboni Bertrand
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500474
Subject(s) - chemistry , tetracyanoethylene , conjugated system , cycloaddition , tosyl , stereoselectivity , amine gas treating , isocyanate , methyl vinyl ketone , aryl , ketone , diels–alder reaction , diene , organic chemistry , combinatorial chemistry , medicinal chemistry , polyurethane , catalysis , polymer , alkyl , natural rubber
A diene‐transmissive hetero‐Diels–Alder reaction of cross‐conjugated 1‐azatrienes (3‐1‐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.