Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values

Date

2016-02-05

Author

Ozer, Merve Sinem
Menges, Nurettin
Keskin, Selbi
ŞAHİN, Ertan
Balcı, Metin

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The AgOTf-catalyzed reaction of C-2 substituted pyrrole hydrazones having an N-propargyl group was studied. The selective 6-endo-dig mode of cyclization was observed, giving rise to the formation of pyrrole-fused C,N-cyclic azomethine imine derivatives. The reaction of one azomethine imine derivative with various dipolarophiles resulted in the formation of cycloadducts having a pyrazolopyrrolopyrazine skeleton. The aromaticity of C,N-cyclic azomethine imines as well as that of pyrazolopyrrolopyrazines was determined by calculating of nucleus-independent chemical shifts values.

Subject Keywords

Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry

URI

https://hdl.handle.net/11511/51312

Journal

ORGANIC LETTERS

DOI

https://doi.org/10.1021/acs.orglett.5b03434

Collections

Graduate School of Natural and Applied Sciences, Article

Citation Formats

M. S. Ozer, N. Menges, S. Keskin, E. ŞAHİN, and M. Balcı, “Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values,” ORGANIC LETTERS, vol. 18, no. 3, pp. 408–411, 2016, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/51312.