Two Cycles with One Catch: Hydrazine in Ugi 4-CR and Its Postcyclizations

Yuanze Wang; Pravin Patil; Katarzyna Kurpiewska; Justyna Kalinowska-Tluscik; Alexander Domling

doi:10.1021/acscombsci.7b00009

Two Cycles with One Catch: Hydrazine in Ugi 4-CR and Its Postcyclizations

Yuanze Wang, Pravin Patil, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Alexander Domling^*

^*Bijbehorende auteur voor dit werk

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Onderzoeksoutput: Article › Academic › peer review

18 Citaten (Scopus)

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Isocyanide-based multicomponent reactions (IMCR) are by far the most versatile reactions that can construct relatively complex molecules by one-pot synthesis. More importantly, the development of post IMCR modifications significantly improves the scaffold's diversity. Here, we describe the use of N-Boc protected hydrazine together with a-amino acid derived isocyanides in the Ugi tetrazole reaction and its post cyclization under both acidic and basic conditions. The cyclization in acidic conditions was conducted in a one pot fashion, which give 7-aminotetrazolopyrazinone (6) and tetrazolotriazepinone (7) cyclic products. The post cyclization under basic condition could selectively afford Boc-protected 7-aminotetrazolopyrazinone (8) products in yield of 38-87%.

Originele taal-2	English
Pagina's (van-tot)	193-198
Aantal pagina's	6
Tijdschrift	Acs combinatorial science
Volume	19
Nummer van het tijdschrift	3
DOI's	https://doi.org/10.1021/acscombsci.7b00009
Status	Published - 13-mrt.-2017

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10.1021/acscombsci.7b00009Licentie: CC BY-NC-ND

Two Cycles with One Catch: Hydrazine in Ugi 4-CR and Its PostcyclizationsFinal publisher's version, 1,52 MBLicentie: CC BY-NC-ND

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Permanente koppeling

CCDC 1507441: Experimental Crystal Structure Determination
Wang, Y. (Contributor), Patil, P. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tluscik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 29-sep.-2016
DOI: 10.5517/ccdc.csd.cc1mlm4z
Dataset
CCDC 1507439: Experimental Crystal Structure Determination
Wang, Y. (Contributor), Patil, P. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tluscik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 29-sep.-2016
DOI: 10.5517/ccdc.csd.cc1mlm2x
Dataset
CCDC 1507084: Experimental Crystal Structure Determination
Wang, Y. (Contributor), Patil, P. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tluscik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 28-sep.-2016
DOI: 10.5517/ccdc.csd.cc1ml7m2
Dataset

Citeer dit

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title = "Two Cycles with One Catch: Hydrazine in Ugi 4-CR and Its Postcyclizations",

abstract = "Isocyanide-based multicomponent reactions (IMCR) are by far the most versatile reactions that can construct relatively complex molecules by one-pot synthesis. More importantly, the development of post IMCR modifications significantly improves the scaffold's diversity. Here, we describe the use of N-Boc protected hydrazine together with a-amino acid derived isocyanides in the Ugi tetrazole reaction and its post cyclization under both acidic and basic conditions. The cyclization in acidic conditions was conducted in a one pot fashion, which give 7-aminotetrazolopyrazinone (6) and tetrazolotriazepinone (7) cyclic products. The post cyclization under basic condition could selectively afford Boc-protected 7-aminotetrazolopyrazinone (8) products in yield of 38-87%.",

keywords = "isocyanide-based multicomponent reactions, hydrazine, post cyclization, tetrazole, one-pot synthesis, scaffolds diversity, European Lead Factory, MULTICOMPONENT REACTIONS, BOC/CYCLIZE STRATEGY, 3-COMPONENT REACTION, SMALL MOLECULES, HETEROCYCLES, ISOCYANIDE, CHEMISTRY, ACIDS",

author = "Yuanze Wang and Pravin Patil and Katarzyna Kurpiewska and Justyna Kalinowska-Tluscik and Alexander Domling",

year = "2017",

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doi = "10.1021/acscombsci.7b00009",

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T2 - Hydrazine in Ugi 4-CR and Its Postcyclizations

AU - Wang, Yuanze

AU - Patil, Pravin

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tluscik, Justyna

AU - Domling, Alexander

PY - 2017/3/13

Y1 - 2017/3/13

N2 - Isocyanide-based multicomponent reactions (IMCR) are by far the most versatile reactions that can construct relatively complex molecules by one-pot synthesis. More importantly, the development of post IMCR modifications significantly improves the scaffold's diversity. Here, we describe the use of N-Boc protected hydrazine together with a-amino acid derived isocyanides in the Ugi tetrazole reaction and its post cyclization under both acidic and basic conditions. The cyclization in acidic conditions was conducted in a one pot fashion, which give 7-aminotetrazolopyrazinone (6) and tetrazolotriazepinone (7) cyclic products. The post cyclization under basic condition could selectively afford Boc-protected 7-aminotetrazolopyrazinone (8) products in yield of 38-87%.

AB - Isocyanide-based multicomponent reactions (IMCR) are by far the most versatile reactions that can construct relatively complex molecules by one-pot synthesis. More importantly, the development of post IMCR modifications significantly improves the scaffold's diversity. Here, we describe the use of N-Boc protected hydrazine together with a-amino acid derived isocyanides in the Ugi tetrazole reaction and its post cyclization under both acidic and basic conditions. The cyclization in acidic conditions was conducted in a one pot fashion, which give 7-aminotetrazolopyrazinone (6) and tetrazolotriazepinone (7) cyclic products. The post cyclization under basic condition could selectively afford Boc-protected 7-aminotetrazolopyrazinone (8) products in yield of 38-87%.

KW - isocyanide-based multicomponent reactions

KW - hydrazine

KW - post cyclization

KW - tetrazole

KW - one-pot synthesis

KW - scaffolds diversity

KW - European Lead Factory

KW - MULTICOMPONENT REACTIONS

KW - BOC/CYCLIZE STRATEGY

KW - 3-COMPONENT REACTION

KW - SMALL MOLECULES

KW - HETEROCYCLES

KW - ISOCYANIDE

KW - CHEMISTRY

KW - ACIDS

U2 - 10.1021/acscombsci.7b00009

DO - 10.1021/acscombsci.7b00009

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JO - Acs combinatorial science

JF - Acs combinatorial science

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ER -

Two Cycles with One Catch: Hydrazine in Ugi 4-CR and Its Postcyclizations

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Datasets

CCDC 1507441: Experimental Crystal Structure Determination

CCDC 1507439: Experimental Crystal Structure Determination

CCDC 1507084: Experimental Crystal Structure Determination

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