General Method for the Preparation of Indole-2-Weinreb Amides

Glas, Carina; Bracher, Franz

doi:10.1055/s-0037-1610660

Synthesis

2018

DOI: 10.1055/s-0037-1610660

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General Method for the Preparation of Indole-2-Weinreb Amides

Carina Glas

Franz Bracher

Abstract: Indole-2-Weinreb amides are obtained via thermolysis of α-azidocinnamic acid Weinreb amides in a Hemetsberger–Knittel-type cyclization. The required vinyl azides are not accessible by Knoevenagel condensation, but are obtained by cerium(IV)-mediated oxidative azidation of the corresponding cinnamic Weinreb amides.

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Cited by 4 publications

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A Novel Approach to Highly Substituted β‐Carbolines via Reductive Ring Transformation of 2‐Acyl‐3‐isoxazolylindoles

Kamlah

Bracher

2020

Eur J Org Chem

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We have worked out a new approach to 1,3,4‐trisubstituted β‐carbolines of pharmaceutical interest. As central building blocks we used 2‐acylindoles, which are readily available from indole‐2‐Weinreb amides. Bromination at C‐3, followed by Suzuki–Miyaura cross‐coupling with isoxazole‐4‐boronates gives 2‐acyl‐3‐isoxazolylindoles. Ring closure to the β‐carbolines was accomplished by reductive ring transformation upon catalytic hydrogenation in the presence of Cs2CO3.

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A Novel Approach to Highly Substituted β‐Carbolines via Reductive Ring Transformation of 2‐Acyl‐3‐isoxazolylindoles

Kamlah

Bracher

2020

Eur J Org Chem

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Advances in 2H-azirine chemistry: A seven-year update

2019

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Nitrobutadienes as powerful benzannulating agents: An unprecedented easy access to rare nitroindoles

et al. 2019

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General Method for the Preparation of Indole-2-Weinreb Amides

Cited by 4 publications

References 28 publications

A Novel Approach to Highly Substituted β‐Carbolines via Reductive Ring Transformation of 2‐Acyl‐3‐isoxazolylindoles

A Novel Approach to Highly Substituted β‐Carbolines via Reductive Ring Transformation of 2‐Acyl‐3‐isoxazolylindoles

Advances in 2H-azirine chemistry: A seven-year update

Nitrobutadienes as powerful benzannulating agents: An unprecedented easy access to rare nitroindoles

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