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

School of Chemistry, Bangor University
PhytoQuest Limited, Aberystwyth
University of Southampton

Allbwn ymchwil: Cyfraniad at gyfnodolyn › Erthygl › adolygiad gan gymheiriaid

381 Wedi eu Llwytho i Lawr (Pure)

Crynodeb

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.

Iaith wreiddiol	Saesneg
Tudalennau (o-i)	845-852
Nifer y tudalennau	8
Cyfnodolyn	Tetrahedron
Cyfrol	73
Rhif cyhoeddi	7
Dyddiad ar-lein cynnar	27 Rhag 2016
Dynodwyr Gwrthrych Digidol (DOIs)	https://doi.org/10.1016/j.tet.2016.12.065
Statws	Cyhoeddwyd - 16 Chwef 2017

Mynediad at Ddogfen

10.1016/j.tet.2016.12.065

2017 Intramolecular epoxide ringLlawysgrif awdur wedi’i dderbyn, 189 KB

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 Ebr 2014, Yn: Tetrahedron. 70, 29, t. 4412-4419
Allbwn ymchwil: Cyfraniad at gyfnodolyn › Erthygl › adolygiad gan gymheiriaid
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 Medi 2013, Yn: Tetrahedron Letters. 54, 49, t. 6716-6718
Allbwn ymchwil: Cyfraniad at gyfnodolyn › Erthygl › adolygiad gan gymheiriaid
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 Rhag 2010, Yn: Tetrahedron Letters. 51, 52, t. 6825-6829
Allbwn ymchwil: Cyfraniad at gyfnodolyn › Erthygl › adolygiad gan gymheiriaid

Dyfynnu hyn

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 Limited",

number = "7",

}

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

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

Crynodeb

Mynediad at Ddogfen

Ôl bys

Allbwn Ymchwil

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.

Dyfynnu hyn