期刊
ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 10, 期 12, 页码 3355-3363出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100580
关键词
Vicinal diol; Iron-catalysis; Pyrrolonaphthoquinone; Utahmycin B; Furanonaphthoquinone
资金
- SERB [EMR/2017/002827]
- CSIR [02(0444)/21/EMR-II]
- Government of India
The study focused on the direct oxidative coupling of vicinal diols with 2-aminonaphthoquinones for the selective synthesis of benzo[f]indole-4,9-diones at a moderate temperature. The environmentally benign iron catalyst was found to effectively oxidize the vicinal diols to alpha-hydroxy carbonyl compounds, resulting in a vast range of pyrrolonaphthoquinones in remarkable yield. Interestingly, the use of 1,2-propanediol led to the selective oxidation of the secondary alcohol group, producing 2-methyl pyrrolonaphthoquinones as the major regioisomer.
Direct oxidative coupling of vicinal diols with 2-aminonaphthoquinones has been studied for the selective synthesis of benzo[f]indole-4,9-diones at a moderate temperature. In the presence of an environmentally benign iron catalyst, the vicinal diols were oxidized to alpha-hydroxy carbonyl compounds. Subsequently, 2-amino naphthoquinone reacted with the resultant alpha-hydroxy carbonyl compound through tandem N-C and C-C bond formation to afford a vast range of pyrrolonaphthoquinones in remarkable yield. Interestingly, when the 1,2-propanediol was used, the secondary alcohol group was oxidized preferably by resulting in the 2-methyl pyrrolonaphthoquinones as the major regioisomer. The synthetic utility of the current strategy was extended for one-step delivery of natural products, such as 3-methyl-1H-benzo[f]indole-4,9-dione (a secondary metabolite isolated from Goniothalamus tapis Miq. with anti-PAF activity), antibiotic utahmycin B (3-methyl-1H-benzo[f]indole-4,9-dione), cytotoxic avicequinone B and anti-viral FNQ3 (2-methyl-naphtho[2,3-b]furan-4,9-dione).
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