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Özer MS, Menges N, Keskin S, et al. Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values. Org Lett. 2016;18(3):408-11doi: 10.1021/acs.orglett.5b03434.
Özer, M. S., Menges, N., Keskin, S., Şahin, E., & Balci, M. (2016). Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values. Organic letters, 18(3), 408-11. https://doi.org/10.1021/acs.orglett.5b03434
Özer, Merve Sinem, et al. "Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values." Organic letters vol. 18,3 (2016): 408-11. doi: https://doi.org/10.1021/acs.orglett.5b03434
Özer MS, Menges N, Keskin S, Şahin E, Balci M. Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values. Org Lett. 2016 Feb 05;18(3):408-11. doi: 10.1021/acs.orglett.5b03434. Epub 2016 Jan 11. PMID: 26752224.
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Org Lett. 2016 Feb 05;18(3):408-11. doi: 10.1021/acs.orglett.5b03434. Epub 2016 Jan 11.

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

Organic letters

Merve Sinem Özer, Nurettin Menges, Selbi Keskin, Ertan Şahin, Metin Balci

Affiliations

  1. Department of Chemistry, Middle East Technical University , 06800 Ankara, Turkey.
  2. Faculty of Pharmacy, Yüzüncü Yil University , 65100 Van, Turkey.
  3. Department of Chemistry, Giresun University , 28100 Giresun, Turkey.
  4. Department of Chemistry, Atatürk University , 25240 Erzurum, Turkey.

PMID: 26752224 DOI: 10.1021/acs.orglett.5b03434

Abstract

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.

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