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

Результат исследований: Вклад в журнал › Статья › рецензирование

9 Цитирования (Scopus)

Аннотация

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.

Язык оригинала	Английский
Страницы (с-по)	1350-1358
Число страниц	9
Журнал	Russian Chemical Bulletin
Том	63
Номер выпуска	6
DOI	https://doi.org/10.1007/s11172-014-0602-y
Состояние	Опубликовано - 1 янв. 2014

Предметные области ASJC Scopus

Chemistry(all)

Предметные области WoS

Химия, Междисциплинарные труды

Ссылки

10.1007/s11172-014-0602-y

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Цитировать

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

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. / 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. В: Russian Chemical Bulletin. 2014 ; Том 63, № 6. стр. 1350-1358.

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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,

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",

}

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, том. 63, № 6, стр. 1350-1358. https://doi.org/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. / 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.

В: Russian Chemical Bulletin, Том 63, № 6, 01.01.2014, стр. 1350-1358.

Результат исследований: Вклад в журнал › Статья › рецензирование

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 -