Hydrazine in the Ugi Tetrazole Reaction

Pravin Patil; Ji Zhang; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling

doi:10.1055/s-0035-1561353

Hydrazine in the Ugi Tetrazole Reaction

Pravin Patil, Ji Zhang, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Alexander Dömling^*

^*Corresponding author for this work

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

28 Citations (Scopus)

116 Downloads (Pure)

Abstract

We describe the hitherto unknown use of N-Boc-protected hydrazine in the Ugi tetrazole reaction to access a library of highly substituted 5-(hydrazinomethyl)-1-methyl-1H-tetrazoles. The reaction is very versatile and good to high yielding. A one-pot, two-step procedure is given.

Original language	English
Pages (from-to)	1122-1130
Number of pages	9
Journal	Synthesis
Volume	48
Issue number	8
DOIs	https://doi.org/10.1055/s-0035-1561353
Publication status	Published - 15-Feb-2016

Keywords

hydrazine
isocyanides
multicomponent reaction
tetrazoles
Ugi reaction
benzyl 4 [2 (tert butoxycarbonyl)hydrazino] 4[1 [2 (1h indol 3 yl)ethyl] 1h tetrazol 5 yl]piperidine 1 carboxylic acid
hydrazine derivative
tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 2 methylpropyl]hydrazine 1 carboxylic acid
tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 2 phenylethyl]hydrazine 1 carboxylic acid
tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 3 methylbutyl]hydrazine 1 carboxylic acid
tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 3 phenylpropyl]hydrazine 1 carboxylic acid
tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl)(cyclohexyl)methyl]hydrazine 1 carboxylic acid
tert butyl 2 [1 (1 phenethyl 1h tetrazol 5 yl)cyclohexyl]hydrazine 1 carboxylic acid
tert butyl 2 [1 [1 benzyl 4 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]piperidin 4 yl]]hydrazine 1 carboxylic acid
tert butyl 2 [1 chloro 2 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]propan 2 yl]hydrazine 1 carboxylic acid
tert butyl 2 [2 [1 (1 methoxy 4 methyl 1 oxopentan 2 yl) 1h tetrazol 5 yl]propan 2 yl]hydrazine 1 carboxylic acid
tert butyl 2 [2 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]butan 2 yl]hydrazine 1 carboxylic acid
tert butyl 2 [2 chloro 1 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]ethyl]hydrazine 1 carboxylic acid
tert butyl 2 [2 methyl 1 (1 phenethyl 1h tetrazol 5 yl)propyl]hydrazine 1 carboxylic acid
tert butyl 2 [3 methyl 1 (1 phenethyl 1h tetrazol 5 yl)butyl]hydrazine 1 carboxylic acid
tert butyl 2 [cyclohexyl (1 phenethyl 1h tetrazol 5 yl)methyl]hydrazine 1 carboxylic acid
tert butyl 2 [cyclohexyl(1 cyclohexyl 1h tetrazol 5 yl)methyl]hydrazine 1 carboxylic acid
tert butyl 2[1 (1 tert butyl 1h tetrazol 5 yl) 3 phenylpropyl]hydrazine 1 carboxylic acid
unclassified drug
article
carbon nuclear magnetic resonance
chemical reaction
deprotection reaction
drug isolation
drug screening
electrospray mass spectrometry
mass spectrometry
one pot synthesis
proton nuclear magnetic resonance
proton transport
supercritical fluid chromatography
Ugi tetrazole reaction

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10.1055/s-0035-1561353

Hydrazine in the Ugi Tetrazole ReactionFinal publisher's version, 607 KBLicence: Taverne

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28 Citations
3 Digital or Visual Products

CCDC 1438135: Experimental Crystal Structure Determination
Patil, P., Zhang, J., Kurpiewska, K., Kalinowska-Tłuścik, J. & Dömling, A., 2016
Research output: Non-textual form › Digital or Visual Products › Academic
CCDC 1438136: Experimental Crystal Structure Determination
Patil, P., Zhang, J., Kurpiewska, K., Kalinowska-Tłuścik, J. & Dömling, A., 2016
Research output: Non-textual form › Digital or Visual Products › Academic
CCDC 1438137: Experimental Crystal Structure Determination
Patil, P., Zhang, J., Kurpiewska, K., Kalinowska-Tłuścik, J. & Dömling, A., 2016
Research output: Non-textual form › Digital or Visual Products › Academic

CCDC 1438137: Experimental Crystal Structure Determination
Patil, P. (Contributor), Zhang, J. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 20-Nov-2015
DOI: 10.5517/cc1k8hjv
Dataset
CCDC 1438135: Experimental Crystal Structure Determination
Patil, P. (Contributor), Zhang, J. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 20-Nov-2015
DOI: 10.5517/cc1k8hgs
Dataset
CCDC 1438136: Experimental Crystal Structure Determination
Patil, P. (Contributor), Zhang, J. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 20-Nov-2015
DOI: 10.5517/cc1k8hht
Dataset

Cite this

@article{539d7505f8f84c3ca96d9570d4589751,

title = "Hydrazine in the Ugi Tetrazole Reaction",

abstract = "We describe the hitherto unknown use of N-Boc-protected hydrazine in the Ugi tetrazole reaction to access a library of highly substituted 5-(hydrazinomethyl)-1-methyl-1H-tetrazoles. The reaction is very versatile and good to high yielding. A one-pot, two-step procedure is given.",

keywords = "hydrazine, isocyanides, multicomponent reaction, tetrazoles, Ugi reaction, benzyl 4 [2 (tert butoxycarbonyl)hydrazino] 4[1 [2 (1h indol 3 yl)ethyl] 1h tetrazol 5 yl]piperidine 1 carboxylic acid, hydrazine derivative, tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 2 methylpropyl]hydrazine 1 carboxylic acid, tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 2 phenylethyl]hydrazine 1 carboxylic acid, tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 3 methylbutyl]hydrazine 1 carboxylic acid, tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 3 phenylpropyl]hydrazine 1 carboxylic acid, tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl)(cyclohexyl)methyl]hydrazine 1 carboxylic acid, tert butyl 2 [1 (1 phenethyl 1h tetrazol 5 yl)cyclohexyl]hydrazine 1 carboxylic acid, tert butyl 2 [1 [1 benzyl 4 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]piperidin 4 yl]]hydrazine 1 carboxylic acid, tert butyl 2 [1 chloro 2 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]propan 2 yl]hydrazine 1 carboxylic acid, tert butyl 2 [2 [1 (1 methoxy 4 methyl 1 oxopentan 2 yl) 1h tetrazol 5 yl]propan 2 yl]hydrazine 1 carboxylic acid, tert butyl 2 [2 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]butan 2 yl]hydrazine 1 carboxylic acid, tert butyl 2 [2 chloro 1 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]ethyl]hydrazine 1 carboxylic acid, tert butyl 2 [2 methyl 1 (1 phenethyl 1h tetrazol 5 yl)propyl]hydrazine 1 carboxylic acid, tert butyl 2 [3 methyl 1 (1 phenethyl 1h tetrazol 5 yl)butyl]hydrazine 1 carboxylic acid, tert butyl 2 [cyclohexyl (1 phenethyl 1h tetrazol 5 yl)methyl]hydrazine 1 carboxylic acid, tert butyl 2 [cyclohexyl(1 cyclohexyl 1h tetrazol 5 yl)methyl]hydrazine 1 carboxylic acid, tert butyl 2[1 (1 tert butyl 1h tetrazol 5 yl) 3 phenylpropyl]hydrazine 1 carboxylic acid, unclassified drug, article, carbon nuclear magnetic resonance, chemical reaction, deprotection reaction, drug isolation, drug screening, electrospray mass spectrometry, mass spectrometry, one pot synthesis, proton nuclear magnetic resonance, proton transport, supercritical fluid chromatography, Ugi tetrazole reaction",

author = "Pravin Patil and Ji Zhang and Katarzyna Kurpiewska and Justyna Kalinowska-T{\l}u{\'s}cik and Alexander D{\"o}mling",

year = "2016",

month = feb,

day = "15",

doi = "10.1055/s-0035-1561353",

language = "English",

volume = "48",

pages = "1122--1130",

journal = "Synthesis",

issn = "0039-7881",

publisher = "GEORG THIEME VERLAG KG",

number = "8",

}

TY - JOUR

T1 - Hydrazine in the Ugi Tetrazole Reaction

AU - Patil, Pravin

AU - Zhang, Ji

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tłuścik, Justyna

AU - Dömling, Alexander

PY - 2016/2/15

Y1 - 2016/2/15

N2 - We describe the hitherto unknown use of N-Boc-protected hydrazine in the Ugi tetrazole reaction to access a library of highly substituted 5-(hydrazinomethyl)-1-methyl-1H-tetrazoles. The reaction is very versatile and good to high yielding. A one-pot, two-step procedure is given.

AB - We describe the hitherto unknown use of N-Boc-protected hydrazine in the Ugi tetrazole reaction to access a library of highly substituted 5-(hydrazinomethyl)-1-methyl-1H-tetrazoles. The reaction is very versatile and good to high yielding. A one-pot, two-step procedure is given.

KW - hydrazine

KW - isocyanides

KW - multicomponent reaction

KW - tetrazoles

KW - Ugi reaction

KW - benzyl 4 [2 (tert butoxycarbonyl)hydrazino] 4[1 [2 (1h indol 3 yl)ethyl] 1h tetrazol 5 yl]piperidine 1 carboxylic acid

KW - hydrazine derivative

KW - tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 2 methylpropyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 2 phenylethyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 3 methylbutyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 3 phenylpropyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl)(cyclohexyl)methyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [1 (1 phenethyl 1h tetrazol 5 yl)cyclohexyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [1 [1 benzyl 4 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]piperidin 4 yl]]hydrazine 1 carboxylic acid

KW - tert butyl 2 [1 chloro 2 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]propan 2 yl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [2 [1 (1 methoxy 4 methyl 1 oxopentan 2 yl) 1h tetrazol 5 yl]propan 2 yl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [2 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]butan 2 yl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [2 chloro 1 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]ethyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [2 methyl 1 (1 phenethyl 1h tetrazol 5 yl)propyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [3 methyl 1 (1 phenethyl 1h tetrazol 5 yl)butyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [cyclohexyl (1 phenethyl 1h tetrazol 5 yl)methyl]hydrazine 1 carboxylic acid

KW - tert butyl 2 [cyclohexyl(1 cyclohexyl 1h tetrazol 5 yl)methyl]hydrazine 1 carboxylic acid

KW - tert butyl 2[1 (1 tert butyl 1h tetrazol 5 yl) 3 phenylpropyl]hydrazine 1 carboxylic acid

KW - unclassified drug

KW - article

KW - carbon nuclear magnetic resonance

KW - chemical reaction

KW - deprotection reaction

KW - drug isolation

KW - drug screening

KW - electrospray mass spectrometry

KW - mass spectrometry

KW - one pot synthesis

KW - proton nuclear magnetic resonance

KW - proton transport

KW - supercritical fluid chromatography

KW - Ugi tetrazole reaction

U2 - 10.1055/s-0035-1561353

DO - 10.1055/s-0035-1561353

M3 - Article

SN - 0039-7881

VL - 48

SP - 1122

EP - 1130

JO - Synthesis

JF - Synthesis

IS - 8

ER -

Hydrazine in the Ugi Tetrazole Reaction

Abstract

Keywords

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Research output

CCDC 1438135: Experimental Crystal Structure Determination

CCDC 1438136: Experimental Crystal Structure Determination

CCDC 1438137: Experimental Crystal Structure Determination

Datasets

CCDC 1438137: Experimental Crystal Structure Determination

CCDC 1438135: Experimental Crystal Structure Determination

CCDC 1438136: Experimental Crystal Structure Determination

Cite this