Synthesis of 5-(het)aryl- and 4,5-di(het)ary1-2-(thio)morpholinopyrimidines from 2-chloropyrimidine via S-N(H) and cross-coupling reactions

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Synthesis of 5-(het)aryl- and 4,5-di(het)ary1-2-(thio)morpholinopyrimidines from 2-chloropyrimidine via S-N(H) and cross-coupling reactions. / Cheprakova, E. M.; Verbitskiy, E. V.; Ezhikova, M. A. et al.
In: Russian Chemical Bulletin, Vol. 63, No. 6, 01.01.2014, p. 1350-1358.

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

BibTeX

@article{1ade6d20a2dd4a0289ae543e721e8b5e,

title = "Synthesis of 5-(het)aryl- and 4,5-di(het)ary1-2-(thio)morpholinopyrimidines from 2-chloropyrimidine via S-N(H) and cross-coupling reactions",

abstract = "It has been shown that various combinations of nucleophilic aromatic substitution of hydrogen (S-N(H)), S-N(ipso) and the microwave-assisted Suzuki cross-coupling reactions are a versatile method for the synthesis of 5-(het)ary1-2-(thio)morpholinopyrimidine and 4,5-di(het)ary1-2(thio)morpholinopyrimidine derivatives. All synthesized pyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H(37)Rv.",

keywords = "antituberculosis activity, cross-coupling, microwave irradiation, morpholine, nucleophilic aromatic substitution of hydrogen, pyrimidines, thiomorpholine",

author = "Cheprakova, {E. M.} and Verbitskiy, {E. V.} and Ezhikova, {M. A.} and Kodess, {M. I.} and Pervova, {M. G.} and Slepukhin, {P. A.} and Toporova, {M. S.} and Kravchenko, {M. A.} and Medvinskiy, {I. D.} and Rusinov, {G. L.} and Charushin, {V. N.}",

year = "2014",

month = jan,

day = "1",

doi = "10.1007/s11172-014-0602-y",

language = "English",

volume = "63",

pages = "1350--1358",

journal = "Russian Chemical Bulletin",

issn = "1066-5285",

publisher = "Springer",

number = "6",

}

RIS

TY - JOUR

T1 - Synthesis of 5-(het)aryl- and 4,5-di(het)ary1-2-(thio)morpholinopyrimidines from 2-chloropyrimidine via S-N(H) and cross-coupling reactions

AU - Cheprakova, E. M.

AU - Verbitskiy, E. V.

AU - Ezhikova, M. A.

AU - Kodess, M. I.

AU - Pervova, M. G.

AU - Slepukhin, P. A.

AU - Toporova, M. S.

AU - Kravchenko, M. A.

AU - Medvinskiy, I. D.

AU - Rusinov, G. L.

AU - Charushin, V. N.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - It has been shown that various combinations of nucleophilic aromatic substitution of hydrogen (S-N(H)), S-N(ipso) and the microwave-assisted Suzuki cross-coupling reactions are a versatile method for the synthesis of 5-(het)ary1-2-(thio)morpholinopyrimidine and 4,5-di(het)ary1-2(thio)morpholinopyrimidine derivatives. All synthesized pyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H(37)Rv.

AB - It has been shown that various combinations of nucleophilic aromatic substitution of hydrogen (S-N(H)), S-N(ipso) and the microwave-assisted Suzuki cross-coupling reactions are a versatile method for the synthesis of 5-(het)ary1-2-(thio)morpholinopyrimidine and 4,5-di(het)ary1-2(thio)morpholinopyrimidine derivatives. All synthesized pyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H(37)Rv.

KW - antituberculosis activity

KW - cross-coupling

KW - microwave irradiation

KW - morpholine

KW - nucleophilic aromatic substitution of hydrogen

KW - pyrimidines

KW - thiomorpholine

UR - http://www.scopus.com/inward/record.url?scp=84924230654&partnerID=8YFLogxK

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000350877500014

U2 - 10.1007/s11172-014-0602-y

DO - 10.1007/s11172-014-0602-y

M3 - Article

AN - SCOPUS:84924230654

VL - 63

SP - 1350

EP - 1358

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 6

ER -

ID: 313581