Intramolecular epoxide ring opening cyclisation reactions involving guanidines

Zainab Al-Shuhaib; Marcel Arndt; Mark Dennis; Daniel Evans; Iestyn Jones; Vera  Leitmann; Patrick Murphy; Dion Roberts; Richard Rowles; Yones K. Sadaghiani; Andrew J.  Thornhill; Robert J. Nash; Jackie Hollinshead; Barbara Bartholomew; Graham Tizzard; Simon Coles

doi:10.1016/j.tet.2016.12.065

Intramolecular epoxide ring opening cyclisation reactions involving guanidines

Zainab Al-Shuhaib, Marcel Arndt, Mark Dennis, Daniel Evans, Iestyn Jones, Vera Leitmann, Patrick Murphy, Dion Roberts, Richard Rowles, Yones K. Sadaghiani, Andrew J. Thornhill, Robert J. Nash, Jackie Hollinshead, Barbara Bartholomew, Graham Tizzard, Simon Coles

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

376 Downloads (Pure)

Abstract

The cyclisation of N-allyl- and N-homoallylguanidines using DMDO leading to the formation of novel 5- and 6-membered guanidine heterocycles is reported. Several of the products formed displayed weak inhibition of glycosidase enzymes.

Original language	English
Pages (from-to)	845-852
Number of pages	8
Journal	Tetrahedron
Volume	73
Issue number	7
Early online date	27 Dec 2016
DOIs	https://doi.org/10.1016/j.tet.2016.12.065
Publication status	Published - 16 Feb 2017

Keywords

guanidines
epoxides
epoxidation
DMDO
iodocyclisations
galactosidase inhibition

Access to Document

10.1016/j.tet.2016.12.065

2017 Intramolecular epoxide ringAccepted author manuscript, 189 KB

5 Article

Iodocyclisations reactions of Boc- and Cbz-protected N-allylguanidines
Al-Shuhaib, Z. A., Al Shuhaiba, Z., Davies, D. H., Dennis, M., Evans, D. M., Fletcher, M. D., Franken, H., Hancock, P., Hollinshead, J., Jones, I., Kähm, K., Murphy, P. J., Nash, R. P. & Rowles, R., 15 Apr 2014, In: Tetrahedron. 70, 29, p. 4412-4419
Research output: Contribution to journal › Article › peer-review
Intramolecular palladium mediated π-allyl cyclisation of bis-Cbz- and bis-Boc-protected guanidines
Al-Shuhaib, Z. A., Doerksen, E., Page, J. M., Al-Shuhaiba, Z., Böckemeier, H., Coghlan, L., Dörksena, E., Jones, I. V., Murphy, P. J. & Nash, R. P., 27 Sept 2013, In: Tetrahedron Letters. 54, 49, p. 6716-6718
Research output: Contribution to journal › Article › peer-review
Iodocyclisation and rearrangement reactions of mono-protected allyl substituted guanidines.
Davies, D., Fletcher, M. D., Franken, H., Hollinshead, J., Kahm, K., Murphy, P. J., Nash, R. & Potter, D. M., 29 Dec 2010, In: Tetrahedron Letters. 51, 52, p. 6825-6829
Research output: Contribution to journal › Article › peer-review

Cite this

Al-Shuhaib, Z., Arndt, M., Dennis, M., Evans, D., Jones, I., Leitmann, V., Murphy, P., Roberts, D., Rowles, R., Sadaghiani, Y. K., Thornhill, A. J., Nash, R. J., Hollinshead, J., Bartholomew, B., Tizzard, G., & Coles, S. (2017). Intramolecular epoxide ring opening cyclisation reactions involving guanidines. Tetrahedron, 73(7), 845-852. https://doi.org/10.1016/j.tet.2016.12.065

@article{80fb4b8fb79d4f298b3ffe638618f406,

title = "Intramolecular epoxide ring opening cyclisation reactions involving guanidines",

abstract = "The cyclisation of N-allyl- and N-homoallylguanidines using DMDO leading to the formation of novel 5- and 6-membered guanidine heterocycles is reported. Several of the products formed displayed weak inhibition of glycosidase enzymes.",

keywords = "guanidines, epoxides, epoxidation, DMDO, iodocyclisations, galactosidase inhibition",

author = "Zainab Al-Shuhaib and Marcel Arndt and Mark Dennis and Daniel Evans and Iestyn Jones and Vera Leitmann and Patrick Murphy and Dion Roberts and Richard Rowles and Sadaghiani, \{Yones K.\} and Thornhill, \{Andrew J.\} and Nash, \{Robert J.\} and Jackie Hollinshead and Barbara Bartholomew and Graham Tizzard and Simon Coles",

year = "2017",

month = feb,

day = "16",

doi = "10.1016/j.tet.2016.12.065",

language = "English",

volume = "73",

pages = "845--852",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "7",

}

TY - JOUR

T1 - Intramolecular epoxide ring opening cyclisation reactions involving guanidines

AU - Al-Shuhaib, Zainab

AU - Arndt, Marcel

AU - Dennis, Mark

AU - Evans, Daniel

AU - Jones, Iestyn

AU - Leitmann, Vera

AU - Murphy, Patrick

AU - Roberts, Dion

AU - Rowles, Richard

AU - Sadaghiani, Yones K.

AU - Thornhill, Andrew J.

AU - Nash, Robert J.

AU - Hollinshead, Jackie

AU - Bartholomew, Barbara

AU - Tizzard, Graham

AU - Coles, Simon

PY - 2017/2/16

Y1 - 2017/2/16

N2 - The cyclisation of N-allyl- and N-homoallylguanidines using DMDO leading to the formation of novel 5- and 6-membered guanidine heterocycles is reported. Several of the products formed displayed weak inhibition of glycosidase enzymes.

AB - The cyclisation of N-allyl- and N-homoallylguanidines using DMDO leading to the formation of novel 5- and 6-membered guanidine heterocycles is reported. Several of the products formed displayed weak inhibition of glycosidase enzymes.

KW - guanidines

KW - epoxides

KW - epoxidation

KW - DMDO

KW - iodocyclisations

KW - galactosidase inhibition

U2 - 10.1016/j.tet.2016.12.065

DO - 10.1016/j.tet.2016.12.065

M3 - Article

SN - 0040-4020

VL - 73

SP - 845

EP - 852

JO - Tetrahedron

JF - Tetrahedron

IS - 7

ER -

Intramolecular epoxide ring opening cyclisation reactions involving guanidines

Abstract

Keywords

Access to Document

Fingerprint

Research output

Iodocyclisations reactions of Boc- and Cbz-protected N-allylguanidines

Intramolecular palladium mediated π-allyl cyclisation of bis-Cbz- and bis-Boc-protected guanidines

Iodocyclisation and rearrangement reactions of mono-protected allyl substituted guanidines.

Cite this