Synthesis of 3‐Amino‐8‐azachromans and 3‐Amino‐7‐azabenzofurans via Inverse Electron Demand Diels–Alder Reaction

The synthesis of 3‐amino‐8‐azachromans and 3‐amino‐7‐azabenzofurans derivatives is reported. The synthetic strategy is based on an inverse electron demand Diels–Alder approach, which employs 1,2,4‐triazines that are judiciously substituted with amino alkynols. This approach permits the variation of...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2009-07, Vol.2009 (21), p.3619-3627
Main Authors: Badarau, Eduard, Suzenet, Franck, Fînaru, Adriana‐Luminiţa, Guillaumet, Gérald
Format: Article
Language:English
Subjects:
Chemistry
Cycloaddition
Exact sciences and technology
Heterocycles
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Polycycles
Preparations and properties
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Summary:The synthesis of 3‐amino‐8‐azachromans and 3‐amino‐7‐azabenzofurans derivatives is reported. The synthetic strategy is based on an inverse electron demand Diels–Alder approach, which employs 1,2,4‐triazines that are judiciously substituted with amino alkynols. This approach permits the variation of the substituent on the aromatic core and on the amine moiety, as well as of the size of the nonaromatic ring.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) A series of chroman isosteres was synthesized by using an intramolecular inverse electron demand Diels–Alder reaction as key step. This approach allows the modulation of the pyridin core of the aminemoiety and of the nonaromatic ring size.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200900191