N' -((1-(Prop-2-yn-1-yl)-1 H -pyrrol-2-yl)methylene)formohydrazide

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

Merve Sinem Özer^†, Nurettin Menges^†‡, Selbi Keskin^†∥, Ertan Şahin^§, and Metin Balci^*†

^† 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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