Expedient Synthesis of α-(2-Azaheteroaryl) Acetates via the Addition of Silyl Ketene Acetals to Azine-<i>N</i>-oxides

Londregan, Allyn T.; Burford, Kristen; Conn, Edward L.; Hesp, Kevin D.

doi:10.1021/ol501359r

Cited by 48 publications

(15 citation statements)

References 32 publications

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“…[135] The strategy involves the use of isoquinoline-N-oxide and different NH-sulfoximines in the presence of PyBroP (bromo tripyrrolidinophosphonium hexafluorophosphate) as the NÀ O bond activating agent, and diisopropylethylamine (DIPEA) as the base (Scheme 54). [136] Good to high yields of corresponding N-arylated products 57 were obtained using several substituted sulfoximines. This reaction is also efficient using various quinolines and pyridines, as well as with 1,10-phenanthroline, 2,2'-bipyridine, and quinine.…”

Section: N-arylationmentioning

confidence: 99%

Synthesis and Transformations of NH‐Sulfoximines

Andresini

Tota

Degennaro

et al. 2021

Chemistry A European J

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Section: N-arylationmentioning

confidence: 99%

Synthesis and Transformations of NH‐Sulfoximines

Andresini

Tota

Degennaro

et al. 2021

Chemistry A European J

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“…One such example is the synthesis of α‐(2‐azaheteroaryl) acetates 207 or 209 from the reaction between 1 and silyl ketene acetals 206 or 208 , respectively, activated by PyBroP (Scheme 61). [87] It should be noted that the hexafluorophosphate counteranion of PyBroP is an important reaction component as it initiates the silicon‐oxygen cleavage necessary for ketene acetal addition.…”

Section: Simple C2‐h‐functionalizationmentioning

confidence: 99%

Recent Advances in the Synthesis of C2‐Functionalized Pyridines and Quinolines Using N‐Oxide Chemistry

et al. 2020

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While remarkable progress has recently been made for the direct C−H‐functionalization of azines, its application is still limited by a lack of accessible functional groups (primarily carbon‐based) and poor regioselectivity. In contrast, C2‐functionalized pyridines and quinolines can be easily synthesized by treating readily available N‐oxides with various reagents under appropriate activation conditions. This review seeks to comprehensively document the available synthetic methods for introducing functional groups at the C2 position of pyridines and quinolines. In this work, we highlight recent developments in the C2‐functionalization of pyridine and quinoline N‐oxides and address both the mechanisms and regioselectivity of the reactions. We also describe the pathways and reactive species involved in these processes and highlight a number of medically relevant nitrogen heteroaromatics.

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“…This procedure afforded several a-(2azaheteroaryl)acetates. 55 Tetrakis-(hydroxymethylene)phosphonium salts ([P(CH 2 OH) 4 ] 1 or THP) have found significant applications in recent years. THP salts exchanged with different anions were widely reported for the production of gels.…”

Section: B P Mes Mes Ph Phmentioning

confidence: 99%