Highly Regioselective Synthesis of 3,6-Diaryl-2-(het)arylpyridines by aza-Diels-Alder Reactions between 6-H-1,2,4-Triazine Dienes and 2-Amino-4-aryloxazole-Based Dienophiles

Standard

Highly Regioselective Synthesis of 3,6-Diaryl-2-(het)arylpyridines by aza-Diels-Alder Reactions between 6-H-1,2,4-Triazine Dienes and 2-Amino-4-aryloxazole-Based Dienophiles. / Shtaitz, Yaroslav k.; Rammohan, Aluru ; Krinochkin, Alexey p. и др.
в: ChemistrySelect, Том 8, № 26, 14.07.2023.

Результаты исследований: Вклад в журнал › Статья › Рецензирование

BibTeX

@article{f2d3210599a84b59936553ee6949bf0b,

title = "Highly Regioselective Synthesis of 3,6-Diaryl-2-(het)arylpyridines by aza-Diels-Alder Reactions between 6-H-1,2,4-Triazine Dienes and 2-Amino-4-aryloxazole-Based Dienophiles",

abstract = "A solvent-free reaction between C6-unsubstituted 5-aryl-1,2,4-triazines and 2-amino-4-aryloxazoles at high temperature was studied. The reaction proceeds via inverse electron demand aza-Diels-Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene with the highly regioselective formation of 3,6-diarylpyridines in up to 60 % isolated yield. The structure of one of the key-products was proven by the X-ray diffraction analysis, and the mechanism of the transformation was proposed. The reaction proceeds well for both 6-aryl and 6-hetaryl-1,2,4-triazines in the presence of the electron acceptor substituent at the position 3. In the case of the donor substituent in position 3, the pyridine yields are significantly reduced. In the case of 5,6-nonsubstituted 1,2,4-triazines, the triazine cycle is degraded without product formation. The high regioselectivity of the reaction as well as solvent-free conditions are valuable advantages of the present synthetic approach.",

author = "Shtaitz, {Yaroslav k.} and Aluru Rammohan and Krinochkin, {Alexey p.} and Ladin, {Evgeny d.} and Butorin, {Ilya i.} and Mochulskaya, {Nataliya n.} and Khalymbadzha, {Igor a.} and Slepukhin, {Pavel a.} and Shevyrin, {Vadim a.} and Kopchuk, {Dmitry s.} and Zyryanov, {Grigory v.} and Chupakhin, {Oleg n.}",

note = "This work was supported by the Ministry of Science and Higher Education of the Russian Federation, Agreement # 075-15-2022-1118 dated 29. 06. 2022. Analytical studies were carried out using equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch).",

year = "2023",

month = jul,

day = "14",

doi = "10.1002/slct.202300903",

language = "English",

volume = "8",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell",

number = "26",

}

RIS

TY - JOUR

T1 - Highly Regioselective Synthesis of 3,6-Diaryl-2-(het)arylpyridines by aza-Diels-Alder Reactions between 6-H-1,2,4-Triazine Dienes and 2-Amino-4-aryloxazole-Based Dienophiles

AU - Shtaitz, Yaroslav k.

AU - Rammohan, Aluru

AU - Krinochkin, Alexey p.

AU - Ladin, Evgeny d.

AU - Butorin, Ilya i.

AU - Mochulskaya, Nataliya n.

AU - Khalymbadzha, Igor a.

AU - Slepukhin, Pavel a.

AU - Shevyrin, Vadim a.

AU - Kopchuk, Dmitry s.

AU - Zyryanov, Grigory v.

AU - Chupakhin, Oleg n.

N1 - This work was supported by the Ministry of Science and Higher Education of the Russian Federation, Agreement # 075-15-2022-1118 dated 29. 06. 2022. Analytical studies were carried out using equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch).

PY - 2023/7/14

Y1 - 2023/7/14

N2 - A solvent-free reaction between C6-unsubstituted 5-aryl-1,2,4-triazines and 2-amino-4-aryloxazoles at high temperature was studied. The reaction proceeds via inverse electron demand aza-Diels-Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene with the highly regioselective formation of 3,6-diarylpyridines in up to 60 % isolated yield. The structure of one of the key-products was proven by the X-ray diffraction analysis, and the mechanism of the transformation was proposed. The reaction proceeds well for both 6-aryl and 6-hetaryl-1,2,4-triazines in the presence of the electron acceptor substituent at the position 3. In the case of the donor substituent in position 3, the pyridine yields are significantly reduced. In the case of 5,6-nonsubstituted 1,2,4-triazines, the triazine cycle is degraded without product formation. The high regioselectivity of the reaction as well as solvent-free conditions are valuable advantages of the present synthetic approach.

AB - A solvent-free reaction between C6-unsubstituted 5-aryl-1,2,4-triazines and 2-amino-4-aryloxazoles at high temperature was studied. The reaction proceeds via inverse electron demand aza-Diels-Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene with the highly regioselective formation of 3,6-diarylpyridines in up to 60 % isolated yield. The structure of one of the key-products was proven by the X-ray diffraction analysis, and the mechanism of the transformation was proposed. The reaction proceeds well for both 6-aryl and 6-hetaryl-1,2,4-triazines in the presence of the electron acceptor substituent at the position 3. In the case of the donor substituent in position 3, the pyridine yields are significantly reduced. In the case of 5,6-nonsubstituted 1,2,4-triazines, the triazine cycle is degraded without product formation. The high regioselectivity of the reaction as well as solvent-free conditions are valuable advantages of the present synthetic approach.

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001026304100001

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85165466315

U2 - 10.1002/slct.202300903

DO - 10.1002/slct.202300903

M3 - Article

VL - 8

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 26

ER -

ID: 41998025