- Total synthesis of 4-azaeudistomin Y1 and analogues by inverse-electron demand diels-alder reactions of 3-aminoindoles with 1,3,5-triazines
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A new inverse-electron-demand Diels-Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-β-carbolines in high yields. Because N1-unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert-butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert-butyl 1H-indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y1, which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel-Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure-activity relationships at the C1-position. Georg Thieme Verlag Stuttgart · New York.
- Xu, Guoxing,Zheng, Lianyou,Dang, Qun,Bai, Xu
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p. 743 - 752
(2013/04/23)
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- Three-component reaction involving metal-free heteroannulation of N-Boc-3-amido indole, aryl aldehydes, and aromatic alkynes under microwave conditions: Synthesis of highly diversified δ-carbolines
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An efficient synthesis toward highly diversified δ-carbolines via one-pot multicomponent reaction using N-Boc-3-amido indoles, aryl aldehydes, and aromatic terminal alkynes under microwave conditions has been described.
- Sharma, Sudhir K.,Mandadapu, Anil K.,Saifuddin, Mohammad,Gupta, Sahaj,Agarwal, Piyush K.,Mandwal, Ashok K.,Gauniyal, Harsh M.,Kundu, Bijoy
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experimental part
p. 6022 - 6024
(2010/11/18)
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