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

E. M. Cheprakova; E. V. Verbitskiy; M. A. Ezhikova; M. I. Kodess; M. G. Pervova; P. A. Slepukhin; M. S. Toporova; M. A. Kravchenko; I. D. Medvinskiy; G. L. Rusinov; V. N. Charushin

doi:10.1007/s11172-014-0602-y

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

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

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9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1350-1358
Number of pages	9
Journal	Russian Chemical Bulletin
Volume	63
Issue number	6
DOIs	https://doi.org/10.1007/s11172-014-0602-y
Publication status	Published - 1 Jan 2014

Keywords

antituberculosis activity
cross-coupling
microwave irradiation
morpholine
nucleophilic aromatic substitution of hydrogen
pyrimidines
thiomorpholine

ASJC Scopus subject areas

Chemistry(all)

WoS ResearchAreas Categories

Chemistry, Multidisciplinary

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10.1007/s11172-014-0602-y

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Cheprakova, E. M., Verbitskiy, E. V., Ezhikova, M. A., Kodess, M. I., Pervova, M. G., Slepukhin, P. A., Toporova, M. S., Kravchenko, M. A., Medvinskiy, I. D., Rusinov, G. L., & Charushin, V. N. (2014). 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. Russian Chemical Bulletin, 63(6), 1350-1358. https://doi.org/10.1007/s11172-014-0602-y

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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,

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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",

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Cheprakova, EM, Verbitskiy, EV, Ezhikova, MA, Kodess, MI, Pervova, MG, Slepukhin, PA, Toporova, MS, Kravchenko, MA, Medvinskiy, ID, Rusinov, GL & Charushin, VN 2014, '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', Russian Chemical Bulletin, vol. 63, no. 6, pp. 1350-1358. https://doi.org/10.1007/s11172-014-0602-y

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

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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 -

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

Keywords

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