Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values
† Department
of Chemistry, Middle East Technical University, 06800 Ankara, Turkey
‡ Faculty
of Pharmacy, Yüzüncü
Yil University, 65100 Van, Turkey
§ Department
of Chemistry, Atatürk University, 25240 Erzurum, Turkey
∥ Department
of Chemistry, Giresun University, 28100 Giresun, Turkey
Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.5b03434
Publication Date (Web): January 11, 2016
Copyright © 2016 American Chemical Society
*E-mail: mbalci@metu.edu.tr.
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.5b03434
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.
see
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.5b03434/suppl_file/ol5b03434_si_001.pdf
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