Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 42, Issue 11, Pages 3704-3713Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202204033
Keywords
diazo compound; N-terminal electrophile; nitroalkane; hydrazone; tetrahydropyridazine
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Funding
- National Natural Sciences Foundation of China [21871044, 22165022]
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A new reaction method has been developed using DBU to promote the reaction between diazo compounds and nitroalkanes, leading to the construction of functionalized hydrazones and tetrahydropyridazines with the structure feature of nitroalkanes. The reaction involves the simultaneous creation of multiple stereocenters using readily available starting materials.
A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted intermolecular addition reaction two molecules of nitroalkanes to diazo compounds has been developed, in which diazo compounds sereve as the efficient N-terminal electrophiles. The reaction provides two new and highly efficient methods for the construction of functionalized hydrazones and tetrahydropyridazines bearing the structure feature of nitroalkanes from readily available starting materials. The reaction involves a sequential intermolecular nucleophilic addition/elimination/intermolecular Aza-Henry reaction/intramolecular cyclization procedure where two or three adjacent stereocenters are created simultaneously in one-pot manner.
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