Bischler–Napieralski Synthesis of Polycyclic N-Heteroaromatics Based on Tf<sub>2</sub>O-Promoted Electrophilic Activation of <i>N</i>-Aryl-2-Propynamides

Four N‐acenoacenes were synthesized and analyzed for their optoelectronic properties and solid‐state packings. Two of the regioisomeric acridinoacridines are TIPS‐ethynylated, whereas the other pair are Boc‐ and triflate substituted derivatives. The two TIPS‐ethynyldiazaacenoacenes were processed into organic thin‐film transistors with saturation hole mobilities reaching 2.9×10−2 cm2(Vs)−1.

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N‐Acenoacenes: Synthesis and Solid‐State Properties

Wiesner

Pardon

Maier

et al. 2022

Chemistry A European J

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Tandem Synthesis of 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones Based on Tf₂O-Promoted Activation of N-(2-Propyn-1-yl) Amides

Shan

Zheng

et al. 2022

J. Org. Chem.

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Structurally novel 2-azaspiro[4.5]deca-1,6,9-trien-8-ones were synthesized from N-(2-propyn-1-yl) amides and 1,3,5-trimethoxybenzenes by a tandem method consisting of a Tf2O-promoted amide activation and a TfOH-promoted Friedel–Crafts ipso-cyclization. The method offered the first example of using N-(2-propyn-1-yl) amides as substrates in both Tf2O-promoted secondary amide activation and the synthesis of azaspiro[4.5]deca-6,9-diene-8-ones.

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Mechanistic Insights into Tf₂O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines

Shan

Zheng

et al. 2022

Org. Lett.

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Bischler–Napieralski Synthesis of Polycyclic N-Heteroaromatics Based on Tf₂O-Promoted Electrophilic Activation of N-Aryl-2-Propynamides

Cited by 5 publications

References 39 publications

N‐Acenoacenes: Synthesis and Solid‐State Properties

N‐Acenoacenes: Synthesis and Solid‐State Properties

Tandem Synthesis of 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones Based on Tf₂O-Promoted Activation of N-(2-Propyn-1-yl) Amides

Mechanistic Insights into Tf₂O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines

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Bischler–Napieralski Synthesis of Polycyclic N-Heteroaromatics Based on Tf2O-Promoted Electrophilic Activation of N-Aryl-2-Propynamides

Cited by 5 publications

References 39 publications

N‐Acenoacenes: Synthesis and Solid‐State Properties

N‐Acenoacenes: Synthesis and Solid‐State Properties

Tandem Synthesis of 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones Based on Tf2O-Promoted Activation of N-(2-Propyn-1-yl) Amides

Mechanistic Insights into Tf2O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines

Contact Info

Product

Resources

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Bischler–Napieralski Synthesis of Polycyclic N-Heteroaromatics Based on Tf₂O-Promoted Electrophilic Activation of N-Aryl-2-Propynamides

Tandem Synthesis of 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones Based on Tf₂O-Promoted Activation of N-(2-Propyn-1-yl) Amides

Mechanistic Insights into Tf₂O-Promoted Electrophilic Activation of 2-Propynamides and a New Synthesis of 2,4-Disubstituted Quinolines