Regioselective Synthesis of Benzo[h][1,6]- naphthyridines and Chromenopyrazinones through Alkyne Cyclization

Date

2017-03-17

Author

Hoplamaz, Emre
KESKİN, SELBİ
Balcı, Metin

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A regioselective approach to the synthesis of benzo[h][1,6]-naphthyridine and chromenopyrazinone derivatives was developed. The synthetic route to benzo[h][1,6]naphthyridines involves the N-propargylation of aromatic aminobenzaldehydes, followed by reaction with propargylamine in the presence of DBU (1,8-diazabicyclo[5.4.0] undec-7ene). For the synthesis of chromenopyrazine and chromeno-pyrazinone derivatives, the acetonitrile group was introduced to salicylaldehyde derivatives, and a DBU-promoted cyclization reaction between aldehydes and propargylamine gave the chromenopyrazines. The intramolecular heterocycloaddition reaction between the triple bond and the azadiene, which is formed as an intermediate, gave the desired structures.

Subject Keywords

Physical and Theoretical Chemistry, Organic Chemistry

URI

https://hdl.handle.net/11511/51578

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1002/ejoc.201601661

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

E. Hoplamaz, S. KESKİN, and M. Balcı, “Regioselective Synthesis of Benzo[h][1,6]- naphthyridines and Chromenopyrazinones through Alkyne Cyclization,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, pp. 1489–1497, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51578.