A Multicomponent Approach toward Angularly Fused/Linear Bitriazoles: A Cascade Cornforth Rearrangement and Triazolization

Santhini Pulikkal Veettil; Shandev Pookkandam Parambil; Max Van Hoof; Wim Dehaen

doi:10.1021/acs.joc.0c03014

A Multicomponent Approach toward Angularly Fused/Linear Bitriazoles: A Cascade Cornforth Rearrangement and Triazolization

The Journal of Organic Chemistry ◽

10.1021/acs.joc.0c03014 ◽

2021 ◽

Vol 86 (5) ◽

pp. 4346-4354 ◽

Cited By ~ 1

Author(s):

Santhini Pulikkal Veettil ◽

Shandev Pookkandam Parambil ◽

Max Van Hoof ◽

Wim Dehaen

Keyword(s):

Cornforth Rearrangement

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Cornforth rearrangement

Name Reactions ◽

10.1007/978-3-662-04835-1_69 ◽

2002 ◽

pp. 84-84

Author(s):

Jie Jack Li

Keyword(s):

Cornforth Rearrangement

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1-(4-Nitrophenyl)-1H-1,2,3-Triazole-4-carbaldehyde: Scalable Synthesis and Its Use in the Preparation of 1-Alkyl-4-Formyl-1,2,3-triazoles

Organics ◽

10.3390/org2040024 ◽

2021 ◽

Vol 2 (4) ◽

pp. 404-414

Author(s):

Tomas Opsomer ◽

Kaat Valkeneers ◽

Ana Ratković ◽

Wim Dehaen

Keyword(s):

One Pot ◽

Complete Hydrolysis ◽

One Step ◽

Synthetic Intermediates ◽

Cornforth Rearrangement ◽

Scalable Synthesis ◽

The One ◽

Novel Applications ◽

Hydrolysis Of

1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide.

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