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Beilstein J. Org. Chem. 2020, 16, 1636–1648, doi:10.3762/bjoc.16.136
Graphical Abstract
Scheme 1: Rearrangement of methylenedioxy-substituted aminoaldehyde 1a to regioisomer 2a and formation of the...
Scheme 2: Synthesis of 1-arylisoindoles 6 and formation of dimers 5.
Scheme 3: Rearrangement of aminoaldehydes 1 to regioisomers 2 and formation of dimer-like products 3 and 8.
Figure 1: X-ray structures of compounds 3b (left) and 8b (right).
Scheme 4: Proposed mechanism of the isomerization of aldehydes 1 via isoindoles 4.
Scheme 5: Proposed mechanism of the formation of dimer-like products 3a,b.
Scheme 6: Proposed mechanism for the formation of dimer-like products 8a,b.
Scheme 7: Dimerization of indole under acidic conditions.
Figure 2: Gibbs free energy diagram for the 1→2 rearrangement.
Scheme 8: Reaction of o-(pivaloylaminomethyl)benzaldehyde (1e) to give dimer-like products 23a and 23b.
Figure 3: X-ray structures of compounds 23a (left) and 23b (right).
Figure 4: Structures of the minimal energy conformer of stereoisomer 23a and those of two minimal energy conf...
Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155
Scheme 1: Synthetic routes to O-thiocarbamates and dithiocarbamates.
Scheme 2: Substrate scope of isocyanides. aReaction conditions: 1 (1 mmol), S8 (2 mmol), 2a (2mmol), NaH (2 m...
Scheme 3: Substrate scope of alcohols. Reaction conditions: 1a (1 mmol), S8 (2 mmol), 2 (2mmol), NaH (2 mmol)...
Scheme 4: Substrate scope of thiols. Reaction conditions: 1a (1 mmol), S8 (1.2 mmol), 4 (2 mmol), NaOH (2 mmo...
Scheme 5: Scaled-up synthesis for 3a.
Scheme 6: Multicomponent domino synthesis of quinazolinone 7.
Scheme 7: Control experiments.
Scheme 8: Proposed mechanism.
Beilstein J. Org. Chem. 2017, 13, 76–86, doi:10.3762/bjoc.13.10
Scheme 1: Synthesis of starting N-benzylideneamines 1.
Scheme 2: Addition of diethyl phosphite to N-benzylidene(butyl)amine in acetonitrile.
Figure 1: IR spectra of the reaction components in acetonitrile solution.
Figure 2: A segment of the time-dependent IR spectrum for the addition of diethyl phosphite to N-benzylidene(...
Figure 3: Concentration profiles of the reaction components in the addition reaction at 80 °C in acetonitrile....
Figure 4: Atomic numbering with anisotropic displacements plot of 5b at −100 °C.
Figure 5: Atomic numbering with anisotropic displacements plot of 5d at −100 °C.
Figure 6: The energy diagram for the reaction with dimethyl phosphite.
Figure 7: The energy diagram for the reaction with diphenylphosphine oxide.