Journal
ORGANIC LETTERS
Volume 24, Issue 6, Pages 1280-1285Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04193
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Funding
- National Natural Science Foundation of China [U2004189]
- Central Plains Science and Technology Innovation Leader Project [224200510009]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [20IRTSTHN005]
- Natural Science Foundation of Henan Province [212300410364]
- Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
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A unique [4+1+1] annulation reaction of N-aryl amidines with diazo homophthalimides and O-2 enables the synthesis of structurally and pharmaceutically attractive spiro [benzo[d][1,3]oxazine-4,4'-isoquinoline] compounds. This unprecedented reaction exhibits readily obtainable substrates, a cost-free and clean oxygen source, a sustainable reaction medium, broad tolerance of functional groups, and an interesting reaction mechanism based on sequential C(sp(2))-H/ C(sp(3))-H bond cleavage and oxygen insertion.
Synthesis of spiro [benzo[d][1,3]oxazine-4,4 '- isoquinoline]s through a unique [4+1+1] annulation of N-aryl amidines with diazo homophthalimides and O-2 is presented. This unprecedented spirocyclization reaction features readily obtainable substrates, structurally and pharmaceutically attractive products, a cost-free and clean oxygen source, sustainable reaction medium, tolerance of a broad spectrum of functional groups, and an interesting reaction mechanism based on sequential C(sp(2))-H/ C(sp(3))-H bond cleavage and oxygen insertion.
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