Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions

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

doi:10.1021/acs.orglett.9b00778

Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions

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

^*Corresponding author for this work

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

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Abstract

The Pomeranz-Fritsch reaction and its Schlittler-Müller modification were successfully applied in the Ugi postcyclization strategy by using orthogonally protected aminoacetaldehyde diethyl acetal and complementary electron rich building blocks. Several scaffolds, including isoquinolines, carboline, alkaloid-like tetrazole-fused tetracyclic compounds, and benzo[ d]azepinone scaffolds, were synthesized in generally moderate to good yield. All our syntheses provide a short MCR-based sequence to novel or otherwise difficult to access scaffolds. Hence, we foresee multiple applications of these synthesis technologies.

Original language	English
Pages (from-to)	3533-3537
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.9b00778
Publication status	Published - 17-May-2019

Keywords

SOLUTION-PHASE PREPARATION
PICTET-SPENGLER REACTION
ASYMMETRIC-SYNTHESIS
BOBBITT SYNTHESIS
UGI
ALKALOIDS
EFFICIENT
MCR
FUNCTIONALIZATION
QUINOLINES

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10.1021/acs.orglett.9b00778Licence: CC BY-NC-ND

Diverse Isoquinoline Scaffolds by Ugi/Pomeranz−Fritsch and Ugi/Schlittler−Müller ReactionsFinal publisher's version, 1.19 MBLicence: CC BY-NC-ND

CCDC 1827865: Experimental Crystal Structure Determination
Wang, Y. (Contributor), Patil, P. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tluscik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 16-Jul-2018
DOI: 10.5517/ccdc.csd.cc1zc1ds
Dataset
CCDC 1573261: Experimental Crystal Structure Determination
Wang, Y. (Contributor), Patil, P. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tluscik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 7-Sep-2017
DOI: 10.5517/ccdc.csd.cc1pt3cz
Dataset
CCDC 1828772: Experimental Crystal Structure Determination
Wang, Y. (Contributor), Patil, P. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tluscik, J. (Contributor) & Dömling, A. (Contributor), University of Groningen, 10-Mar-2018
DOI: 10.5517/ccdc.csd.cc1zcznz
Dataset

Cite this

@article{385c7082d5104cca807f937a9bbb4327,

title = "Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-M{\"u}ller Reactions",

abstract = "The Pomeranz-Fritsch reaction and its Schlittler-M{\"u}ller modification were successfully applied in the Ugi postcyclization strategy by using orthogonally protected aminoacetaldehyde diethyl acetal and complementary electron rich building blocks. Several scaffolds, including isoquinolines, carboline, alkaloid-like tetrazole-fused tetracyclic compounds, and benzo[ d]azepinone scaffolds, were synthesized in generally moderate to good yield. All our syntheses provide a short MCR-based sequence to novel or otherwise difficult to access scaffolds. Hence, we foresee multiple applications of these synthesis technologies.",

keywords = "SOLUTION-PHASE PREPARATION, PICTET-SPENGLER REACTION, ASYMMETRIC-SYNTHESIS, BOBBITT SYNTHESIS, UGI, ALKALOIDS, EFFICIENT, MCR, FUNCTIONALIZATION, QUINOLINES",

author = "Yuanze Wang and Pravin Patil and Katarzyna Kurpiewska and Justyna Kalinowska-Tluscik and Alexander D{\"o}mling",

year = "2019",

month = may,

day = "17",

doi = "10.1021/acs.orglett.9b00778",

language = "English",

volume = "21",

pages = "3533--3537",

journal = "Org.Lett.",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

number = "10",

}

TY - JOUR

T1 - Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions

AU - Wang, Yuanze

AU - Patil, Pravin

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tluscik, Justyna

AU - Dömling, Alexander

PY - 2019/5/17

Y1 - 2019/5/17

N2 - The Pomeranz-Fritsch reaction and its Schlittler-Müller modification were successfully applied in the Ugi postcyclization strategy by using orthogonally protected aminoacetaldehyde diethyl acetal and complementary electron rich building blocks. Several scaffolds, including isoquinolines, carboline, alkaloid-like tetrazole-fused tetracyclic compounds, and benzo[ d]azepinone scaffolds, were synthesized in generally moderate to good yield. All our syntheses provide a short MCR-based sequence to novel or otherwise difficult to access scaffolds. Hence, we foresee multiple applications of these synthesis technologies.

AB - The Pomeranz-Fritsch reaction and its Schlittler-Müller modification were successfully applied in the Ugi postcyclization strategy by using orthogonally protected aminoacetaldehyde diethyl acetal and complementary electron rich building blocks. Several scaffolds, including isoquinolines, carboline, alkaloid-like tetrazole-fused tetracyclic compounds, and benzo[ d]azepinone scaffolds, were synthesized in generally moderate to good yield. All our syntheses provide a short MCR-based sequence to novel or otherwise difficult to access scaffolds. Hence, we foresee multiple applications of these synthesis technologies.

KW - SOLUTION-PHASE PREPARATION

KW - PICTET-SPENGLER REACTION

KW - ASYMMETRIC-SYNTHESIS

KW - BOBBITT SYNTHESIS

KW - UGI

KW - ALKALOIDS

KW - EFFICIENT

KW - MCR

KW - FUNCTIONALIZATION

KW - QUINOLINES

U2 - 10.1021/acs.orglett.9b00778

DO - 10.1021/acs.orglett.9b00778

M3 - Article

C2 - 31033297

VL - 21

SP - 3533

EP - 3537

JO - Org.Lett.

JF - Org.Lett.

SN - 1523-7060

IS - 10

ER -

Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions

Abstract

Keywords

Access to Document

Datasets

CCDC 1827865: Experimental Crystal Structure Determination

CCDC 1573261: Experimental Crystal Structure Determination

CCDC 1828772: Experimental Crystal Structure Determination

Cite this