Application of cyclic ketones in MCR: Ugi/amide coupling based synthesis of fused tetrazolo[1,5-a][1,4]benzodiazepines

Swapnil Yerande; Kiran Newase; Bhawani Singh; André Boltjes; Alex Dömling

doi:10.1016/j.tetlet.2014.04.040

Application of cyclic ketones in MCR: Ugi/amide coupling based synthesis of fused tetrazolo[1,5-a][1,4]benzodiazepines

Swapnil Yerande, Kiran Newase, Bhawani Singh, André Boltjes, Alex Dömling

Research output: Contribution to journal › Article › Academic › peer-review

21 Citations (Scopus)

Abstract

Azido-Ugi reaction involving cyclic ketone, primary amine, isonitrile, and azide afforded substituted tetrazole derivatives 5. These intermediates were hydrolyzed to corresponding acid derivatives. EDAC/HOBt mediated amide bond formation of 5 gave fused tetrazolo[1,5-a][1,4]benzodiazepine 6 in high yield and good diversity. © 2014 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3263-3266
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2014.04.040
Publication status	Published - 21-May-2014

Keywords

Cyclic ketone
Ugi multi component reaction

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abstract = "Azido-Ugi reaction involving cyclic ketone, primary amine, isonitrile, and azide afforded substituted tetrazole derivatives 5. These intermediates were hydrolyzed to corresponding acid derivatives. EDAC/HOBt mediated amide bond formation of 5 gave fused tetrazolo[1,5-a][1,4]benzodiazepine 6 in high yield and good diversity. {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

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AU - Yerande, Swapnil

AU - Newase, Kiran

AU - Singh, Bhawani

AU - Boltjes, André

AU - Dömling, Alex

PY - 2014/5/21

Y1 - 2014/5/21

N2 - Azido-Ugi reaction involving cyclic ketone, primary amine, isonitrile, and azide afforded substituted tetrazole derivatives 5. These intermediates were hydrolyzed to corresponding acid derivatives. EDAC/HOBt mediated amide bond formation of 5 gave fused tetrazolo[1,5-a][1,4]benzodiazepine 6 in high yield and good diversity. © 2014 Elsevier Ltd. All rights reserved.

AB - Azido-Ugi reaction involving cyclic ketone, primary amine, isonitrile, and azide afforded substituted tetrazole derivatives 5. These intermediates were hydrolyzed to corresponding acid derivatives. EDAC/HOBt mediated amide bond formation of 5 gave fused tetrazolo[1,5-a][1,4]benzodiazepine 6 in high yield and good diversity. © 2014 Elsevier Ltd. All rights reserved.

KW - Cyclic ketone

KW - Ugi multi component reaction

U2 - 10.1016/j.tetlet.2014.04.040

DO - 10.1016/j.tetlet.2014.04.040

M3 - Article

SN - 0040-4039

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SP - 3263

EP - 3266

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Application of cyclic ketones in MCR: Ugi/amide coupling based synthesis of fused tetrazolo[1,5-a][1,4]benzodiazepines

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Keywords

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