'Atypical Ugi' tetrazoles

Eman M M Abdelraheem; Imogen Goodwin; Shabnam Shaabani; Michel P de Haan; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling

doi:10.1039/c9cc09194g

'Atypical Ugi' tetrazoles

Eman M M Abdelraheem, Imogen Goodwin, Shabnam Shaabani, Michel P de Haan, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Alexander Dömling^*

^*Bijbehorende auteur voor dit werk

Onderzoeksoutput › Academic › peer review

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Amino acid-derived isocyano amides together with TMSN3, oxocomponents and 1° or 2° amines are common substrates in the Ugi tetrazole reaction. We surprisingly found that combining these substrates gives two different constitutional isomeric Ugi products A and B. A is the expected classical Ugi product whereas B is an isomeric product ('atypical Ugi') of the same molecular weight with the tetrazole heterocycle migrated to a different position. We synthesized, separated and characterized 22 different isomorphic examples of the two constitutional isomers of the Ugi reaction to unambiguously prove the formation of A and B. Mechanistic studies resulted in a proposed mechanism for the concomitant formation of A and B.

Originele taal-2	English
Pagina's (van-tot)	1799-1802
Aantal pagina's	4
Tijdschrift	Chemical communications (Cambridge, England)
Volume	56
Nummer van het tijdschrift	12
Vroegere onlinedatum	17-jan.-2020
DOI's	https://doi.org/10.1039/c9cc09194g
Status	Published - 11-feb.-2020

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CCDC 1844786: Experimental Crystal Structure Determination
Abdelraheem, E. (Contributor), Goodwin, I. (Contributor), Shaabani, S. (Contributor), Haan , de, M. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 22-mei-2018
DOI: 10.5517/ccdc.csd.cc1zxn7s
Dataset
CCDC 1842386: Experimental Crystal Structure Determination
Abdelraheem, E. (Contributor), Goodwin, I. (Contributor), Shaabani, S. (Contributor), Haan , de, M. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 9-mei-2018
DOI: 10.5517/ccdc.csd.cc1zv4ts
Dataset
CCDC 1844784: Experimental Crystal Structure Determination
Abdelraheem, E. (Contributor), Goodwin, I. (Contributor), Shaabani, S. (Contributor), Haan , de, M. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 22-mei-2018
DOI: 10.5517/ccdc.csd.cc1zxn5q
Dataset

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title = "'Atypical Ugi' tetrazoles",

abstract = "Amino acid-derived isocyano amides together with TMSN3, oxocomponents and 1° or 2° amines are common substrates in the Ugi tetrazole reaction. We surprisingly found that combining these substrates gives two different constitutional isomeric Ugi products A and B. A is the expected classical Ugi product whereas B is an isomeric product ('atypical Ugi') of the same molecular weight with the tetrazole heterocycle migrated to a different position. We synthesized, separated and characterized 22 different isomorphic examples of the two constitutional isomers of the Ugi reaction to unambiguously prove the formation of A and B. Mechanistic studies resulted in a proposed mechanism for the concomitant formation of A and B.",

author = "Abdelraheem, {Eman M M} and Imogen Goodwin and Shabnam Shaabani and {de Haan}, {Michel P} and Katarzyna Kurpiewska and Justyna Kalinowska-T{\l}u{\'s}cik and Alexander D{\"o}mling",

year = "2020",

month = feb,

day = "11",

doi = "10.1039/c9cc09194g",

language = "English",

volume = "56",

pages = "1799--1802",

journal = "Chemical Communications (Cambridge, United Kingdom)",

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T1 - 'Atypical Ugi' tetrazoles

AU - Abdelraheem, Eman M M

AU - Goodwin, Imogen

AU - Shaabani, Shabnam

AU - de Haan, Michel P

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tłuścik, Justyna

AU - Dömling, Alexander

PY - 2020/2/11

Y1 - 2020/2/11

N2 - Amino acid-derived isocyano amides together with TMSN3, oxocomponents and 1° or 2° amines are common substrates in the Ugi tetrazole reaction. We surprisingly found that combining these substrates gives two different constitutional isomeric Ugi products A and B. A is the expected classical Ugi product whereas B is an isomeric product ('atypical Ugi') of the same molecular weight with the tetrazole heterocycle migrated to a different position. We synthesized, separated and characterized 22 different isomorphic examples of the two constitutional isomers of the Ugi reaction to unambiguously prove the formation of A and B. Mechanistic studies resulted in a proposed mechanism for the concomitant formation of A and B.

AB - Amino acid-derived isocyano amides together with TMSN3, oxocomponents and 1° or 2° amines are common substrates in the Ugi tetrazole reaction. We surprisingly found that combining these substrates gives two different constitutional isomeric Ugi products A and B. A is the expected classical Ugi product whereas B is an isomeric product ('atypical Ugi') of the same molecular weight with the tetrazole heterocycle migrated to a different position. We synthesized, separated and characterized 22 different isomorphic examples of the two constitutional isomers of the Ugi reaction to unambiguously prove the formation of A and B. Mechanistic studies resulted in a proposed mechanism for the concomitant formation of A and B.

U2 - 10.1039/c9cc09194g

DO - 10.1039/c9cc09194g

M3 - Article

C2 - 31950120

VL - 56

SP - 1799

EP - 1802

JO - Chemical Communications (Cambridge, United Kingdom)

JF - Chemical Communications (Cambridge, United Kingdom)

SN - 1359-7345

IS - 12

ER -

'Atypical Ugi' tetrazoles

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CCDC 1844786: Experimental Crystal Structure Determination

CCDC 1842386: Experimental Crystal Structure Determination

CCDC 1844784: Experimental Crystal Structure Determination

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