Direct Synthesis for Benzofuro[3,2‐<i>d</i>]pyrimidin‐2‐Amines via One‐Pot Cascade [4+2] Annulation/Aromatization between Benzofuran‐Derived Azadienes and Carbodiimide Anions
The chemoselective [4+2] annulation/aromatization reactions between benzofuran-derived azadienes and N-Ts cyanamides are developed, affording a convenient method for synthesizing benzofuro[3,2-d]pyrimidin-2-amines under mild conditions. Herein, N-Ts cyanamides participated in reactions selectively via carbodiimide anion intermediates and the corresponding cyanamide anion intermediates derived products were not observed. The proposed chemoselective stepwise reaction mechanism was well supported by DFT calculations.
Authors
- Chuan‐Chuan Wang
- Yihui Li (ORCID: https://orcid.org/0000-0002-5562-0907)
- Zhiwei Ma (ORCID: https://orcid.org/0000-0002-4589-6387)
- Xue‐Hui Hou
- Mengru Ren
- Qinglong Wang (ORCID: https://orcid.org/0000-0002-5051-3619)
- Yajing Chen (ORCID: https://orcid.org/0000-0002-1624-0741)
- Xuehua Liu
Institutions
- Henan University (CN)
- Zhengzhou University (CN)
- Henan Agricultural University (CN)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2024-08-30
- DOI
- https://doi.org/10.1002/chem.202402886
- Citations
- 5
- Primary Topic
- Synthesis and Reactivity of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- National Natural Science Foundation of China
- Shanghai University of Traditional Chinese Medicine