Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade

Steven Gunawan; Christopher Hulme

doi:10.1016/j.tetlet.2013.06.042

Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade

Steven Gunawan, Christopher Hulme

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

13 Scopus citations

Abstract

Dihydropyrazino-quinazolinedione chemotypes are complex and structurally challenging structures of biological interest, being found in the marine alkaloids such as brevianamide M-N and fumiquinazolines A-C. Herein we report the synthesis of this tricyclic system in three synthetic operations by means of an Ugi multi-component reaction (MCR) followed by a tandem N-acyliminium ion cyclization-intramolecular nucleophilic addition reaction sequence. Additional structural diversification for further library enrichment was also accomplished via sequential N-alkylation and N-acylation/sulfonation.

Original language	English (US)
Pages (from-to)	4467-4470
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2013.06.042
State	Published - Aug 14 2013

Keywords

Heterocycles
Multi-component reaction
N-acyliminium ion
Peptidomimetics
Ugi reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2013.06.042

Cite this

@article{3489c093dfc8425bb1885fb1b3bd01ce,

title = "Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade",

abstract = "Dihydropyrazino-quinazolinedione chemotypes are complex and structurally challenging structures of biological interest, being found in the marine alkaloids such as brevianamide M-N and fumiquinazolines A-C. Herein we report the synthesis of this tricyclic system in three synthetic operations by means of an Ugi multi-component reaction (MCR) followed by a tandem N-acyliminium ion cyclization-intramolecular nucleophilic addition reaction sequence. Additional structural diversification for further library enrichment was also accomplished via sequential N-alkylation and N-acylation/sulfonation.",

keywords = "Heterocycles, Multi-component reaction, N-acyliminium ion, Peptidomimetics, Ugi reaction",

author = "Steven Gunawan and Christopher Hulme",

note = "Funding Information: The authors thank Dr. Sue Roberts for X-ray crystallography work, Drs. Fabio De Moliner and David M. Bishop for proofreading, and the National Institutes of Health ( P41GM086190 ) for financial support.",

year = "2013",

month = aug,

day = "14",

doi = "10.1016/j.tetlet.2013.06.042",

language = "English (US)",

volume = "54",

pages = "4467--4470",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "33",

}

TY - JOUR

T1 - Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade

AU - Gunawan, Steven

AU - Hulme, Christopher

N1 - Funding Information: The authors thank Dr. Sue Roberts for X-ray crystallography work, Drs. Fabio De Moliner and David M. Bishop for proofreading, and the National Institutes of Health ( P41GM086190 ) for financial support.

PY - 2013/8/14

Y1 - 2013/8/14

N2 - Dihydropyrazino-quinazolinedione chemotypes are complex and structurally challenging structures of biological interest, being found in the marine alkaloids such as brevianamide M-N and fumiquinazolines A-C. Herein we report the synthesis of this tricyclic system in three synthetic operations by means of an Ugi multi-component reaction (MCR) followed by a tandem N-acyliminium ion cyclization-intramolecular nucleophilic addition reaction sequence. Additional structural diversification for further library enrichment was also accomplished via sequential N-alkylation and N-acylation/sulfonation.

AB - Dihydropyrazino-quinazolinedione chemotypes are complex and structurally challenging structures of biological interest, being found in the marine alkaloids such as brevianamide M-N and fumiquinazolines A-C. Herein we report the synthesis of this tricyclic system in three synthetic operations by means of an Ugi multi-component reaction (MCR) followed by a tandem N-acyliminium ion cyclization-intramolecular nucleophilic addition reaction sequence. Additional structural diversification for further library enrichment was also accomplished via sequential N-alkylation and N-acylation/sulfonation.

KW - Heterocycles

KW - Multi-component reaction

KW - N-acyliminium ion

KW - Peptidomimetics

KW - Ugi reaction

UR - http://www.scopus.com/inward/record.url?scp=84880034942&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880034942&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2013.06.042

DO - 10.1016/j.tetlet.2013.06.042

M3 - Article

AN - SCOPUS:84880034942

SN - 0040-4039

VL - 54

SP - 4467

EP - 4470

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this