Journal
TETRAHEDRON LETTERS
Volume 83, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153426
Keywords
3-Carboxamide oxindole; delta-Lactam; Spirooxindole; Trifluoromethyl
Categories
Funding
- National Natural Science Foundation of China [21602114, 22001217]
- Science and Technology Program of Sichuan Province [2018JY0485]
- Meritocracy Research Funds of China West Normal University [17YC020]
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A range of structurally novel CF3-containing spiro-delta-lactam oxindoles were successfully synthesized via the Michael/N-hemiketalization cascade reaction, with moderate to good yields and excellent diastereoselectivities. This work represents the first systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles.
A simple and efficient strategy has been established for the synthesis of delta-lactam fused oxindoles via the Michael/N-hemiketalization cascade reaction of 3-carboxamide oxindoles and alpha,beta-unsaturated trifluoromethyl ketones. A wide range of structurally novel CF3-containing spiro-delta-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atoms were obtained in moderate to good yields with excellent diastereoselectivities under mild conditions. This work represents the first example of a systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles. (C) 2021 Elsevier Ltd. All rights reserved.
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