New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines

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New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines. / Vorob’ev, Aleksey Yu; Supranovich, Vyacheslav I.; Borodkin, Gennady I. et al.

In: Beilstein Journal of Organic Chemistry, Vol. 13, 02.05.2017, p. 800-805.

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

BibTeX

@article{4cde95a12f9b4fd2ac17dbc64eac90da,

title = "New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines",

abstract = "An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D2O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivity and a high degree of deuterium incorporation were achieved. The procedure was applied for several 4-R-1-aminopyridinium cations (R = H, Me, OMe).",

keywords = "1,2,4-triazolo[1,5-a]pyridine, 1,3-dipolar cycloaddition, 3-dipolar cycloaddition, Deuteration, pyrazolo[1,5-a]pyridine, N-IMINOPYRIDINIUM YLIDES, deuteration, DESIGN, DRUG DISCOVERY, RECEPTOR, DEUTERIUM, POTENT, PHARMACOLOGY, AGENTS, INHIBITORS",

author = "Vorob{\textquoteright}ev, {Aleksey Yu} and Supranovich, {Vyacheslav I.} and Borodkin, {Gennady I.} and Shubin, {Vyacheslav G.}",

note = "Publisher Copyright: {\textcopyright} 2017 Vorob{\textquoteright}ev et al.",

year = "2017",

month = may,

day = "2",

doi = "10.3762/bjoc.13.80",

language = "English",

volume = "13",

pages = "800--805",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - New approach toward the synthesis of deuterated pyrazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]pyridines

AU - Vorob’ev, Aleksey Yu

AU - Supranovich, Vyacheslav I.

AU - Borodkin, Gennady I.

AU - Shubin, Vyacheslav G.

PY - 2017/5/2

Y1 - 2017/5/2

N2 - An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D2O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivity and a high degree of deuterium incorporation were achieved. The procedure was applied for several 4-R-1-aminopyridinium cations (R = H, Me, OMe).

AB - An efficient and operationally simple synthesis of 7-deuteropyrazolo[1,5-a]pyridine and 7-deutero-1,2,4-triazolo[1,5-a]pyridine derivatives using α-H/D exchange of 1-aminopyridinium cations in basic D2O followed by a 1,3-cycloaddition of acetylenes and nitriles is presented. A high regioselectivity and a high degree of deuterium incorporation were achieved. The procedure was applied for several 4-R-1-aminopyridinium cations (R = H, Me, OMe).

KW - 1,2,4-triazolo[1,5-a]pyridine

KW - 1,3-dipolar cycloaddition

KW - 3-dipolar cycloaddition

KW - Deuteration

KW - pyrazolo[1,5-a]pyridine

KW - N-IMINOPYRIDINIUM YLIDES

KW - deuteration

KW - DESIGN

KW - DRUG DISCOVERY

KW - RECEPTOR

KW - DEUTERIUM

KW - POTENT

KW - PHARMACOLOGY

KW - AGENTS

KW - INHIBITORS

UR - http://www.scopus.com/inward/record.url?scp=85020773061&partnerID=8YFLogxK

U2 - 10.3762/bjoc.13.80

DO - 10.3762/bjoc.13.80

M3 - Article

AN - SCOPUS:85020773061

VL - 13

SP - 800

EP - 805

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 9049285