Jonathan R. Scheerer
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View article: Synthesis of 2-Azaanthraquinones from 1,4-Oxazinone Precursors
Synthesis of 2-Azaanthraquinones from 1,4-Oxazinone Precursors Open
The synthesis of 2-azaanthraquinone structures from 1,4-oxazinone precursors is described. A new method for the synthesis of 1,4-oxazinones is also reported. The key discovery is the reaction of oxazinone and quinone starting materials thr…
View article: Polysubstituted Pyridines from 1,4-Oxazinone Precursors
Polysubstituted Pyridines from 1,4-Oxazinone Precursors Open
This study describes a general method for the preparation of 1,4-oxazin-2-one intermediates from acetylene dicarboxylate and β-amino alcohol precursors. Oxazinones prepared in this manner were employed in a tandem cycloaddition/cyclorevers…
View article: Construction of the 4-Azafluorenone Core in a Single Operation and Synthesis of Onychine
Construction of the 4-Azafluorenone Core in a Single Operation and Synthesis of Onychine Open
This study describes the synthesis of the 4-azafluorenone core in a single operation using readily available starting materials. Condensation of an amidrazone with ninhydrin intercepts an intermediate 1,2,4-triazine derivative, which engag…
View article: Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone
Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone Open
A new method to prepare 1,4-oxazinone intermediates was developed based on aza-conjugate addition of β-amino alcohols to electron-deficient alkyne precursors. A tandem intramolecular cycloaddition/cycloreversion reaction sequence was evalu…
View article: A Nonoxidative Sequence for the Preparation of 1,2-Diketone Derivatives Using Aldehyde and Organometallic Building Blocks
A Nonoxidative Sequence for the Preparation of 1,2-Diketone Derivatives Using Aldehyde and Organometallic Building Blocks Open
This study investigates a synthetic sequence for the preparation of 1,2-diketone products. The sequence avoids oxidative conditions and instead employs reliable transformations including the Horner-Wadsworth-Emmons and addition of Grignard…
View article: Application of 1,4-Oxazinone Precursors to the Construction of Pyridine Derivatives by Tandem Intermolecular Cycloaddition/Cycloreversion
Application of 1,4-Oxazinone Precursors to the Construction of Pyridine Derivatives by Tandem Intermolecular Cycloaddition/Cycloreversion Open
This study reveals a new method for the preparation of 1,4-oxazinone derivatives by Staudinger reductive cyclization of functionalized vinyl azide precursors. The resulting oxazinone derivatives prepared in this manner were intercepted wit…
View article: Synthesis and Spectrophotometric Analysis of 1-Azafluorenone Derivatives
Synthesis and Spectrophotometric Analysis of 1-Azafluorenone Derivatives Open
A new extension for the ‘one pot’ construction of diverse 1-azafluorene derivatives featuring a Diels–Alder/retro-Diels–Alder cycloaddition is reported. Conditions were also determined for oxidation to the derived azafluorenones. The spect…
View article: Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine
Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine Open
This study reveals an alternative sequence for the synthesis of compounds that contain the pyrrolodiketopiperazine structural motif. Starting with a diketopiperazine precursor, a mild aldol condensation precedes pyrrole annulation and bicy…
View article: Spectroscopic Evidence for Lactam Formation in Terminal Ornithine b<sub>2</sub><sup>+</sup> and b<sub>3</sub><sup>+</sup> Fragment Ions
Spectroscopic Evidence for Lactam Formation in Terminal Ornithine b<sub>2</sub><sup>+</sup> and b<sub>3</sub><sup>+</sup> Fragment Ions Open
Infrared multiple photon dissociation action spectroscopy was performed on the AlaOrn b2+ and AlaAlaOrn b3+ fragment ions from ornithine-containing tetrapeptides. Infrared spectra were obtained i…
View article: Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2-Pyridone Alkaloids
Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2-Pyridone Alkaloids Open
A new domino reaction sequence for the construction of 2-pyridone structures is reported. The reaction sequence begins with diacetyldiketopiperazine and proceeds via aldol condensation, alkene isomerization, and intramolecular Diels-Alder …
View article: CCDC 1814999: Experimental Crystal Structure Determination
CCDC 1814999: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Further Investigation of the Intermolecular Diels–Alder Cycloaddition for the Synthesis of Bicyclo[2.2.2]diazaoctane Alkaloids
Further Investigation of the Intermolecular Diels–Alder Cycloaddition for the Synthesis of Bicyclo[2.2.2]diazaoctane Alkaloids Open
The convergent synthesis of bicyclo[2.2.2]diazaoctane structures using an intermolecular Diels-Alder cycloaddition between a pyrazinone and commercially available fumarate or maleate precursors is reported. High reactivity and stereoselect…
View article: A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines
A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines Open
A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Di…
View article: Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin
Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin Open
Synthesis of barettin, a selective serotonin receptor inhibitor and potent antibiofouling natural product.
View article: 3,4- and 3,5-disubstituted 2-pyridones using an intermolecular cycloaddition/cycloreversion strategy: toward the synthesis of aristopyridinone A
3,4- and 3,5-disubstituted 2-pyridones using an intermolecular cycloaddition/cycloreversion strategy: toward the synthesis of aristopyridinone A Open