Regioselective Syntheses of 2,3,5-Trisubstituted Pyridines via 5-Chloro-3-fluoro-2-(methylsulfonyl)pyridine

被引：1

作者：

Wiley, Robert E. ^{[1
,2
]}

Holan, Martin ^{[1
]}

Kim, Wan Shin ^{[1
]}

Nguyen, Khoa D. ^{[1
,3
]}

Zeng, Xingzhong ^{[1
,3
]}

Krawiec, Mariusz ^{[4
]}

Brusoe, Andrew T. ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Chem Dev, Ridgefield, CT 06877 USA

[2] Univ North Carolina Chapel Hill, Dept Chem, Chapel Hill, NC 27599 USA

[3] Vertex Pharmaceut Inc, 50 Northern Ave, Boston, MA 02210 USA

[4] Boehringer Ingelheim Pharmaceut Inc, Mat & Analyt Sci, Ridgefield, CT 06877 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 11期

关键词：

LATE-STAGE FUNCTIONALIZATION; C-H BORYLATION; SUBSTITUTION; CONSTRUCTION; RING;

D O I：

10.1021/acs.joc.4c00753

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the high-yielding, large-scale, one-pot synthesis of two versatile building blocks (1-Cl and 1-Br) for the regioselective synthesis of a variety of 2,3,5-trisubstituted pyridines from inexpensive materials. These molecules are readily derivatized at positions 2, 3, and 5. These building blocks can also be used for the synthesis of fused pyrido-oxazines and for the synthesis of 2,3,4,5-tetrasubstituted pyridines.

引用

页码：8299 / 8304

页数：6

共 50 条

[1] 2,3,5-TRISUBSTITUTED ALKOXY, ACETOXY AND HYDROXY DERIVATIVES OF PYRIDINE
KROWICKI, K
ROCZNIKI CHEMII, 1976, 50 (10): : 1785 - 1790
[2] NITRATION OF 2,3,5-TRISUBSTITUTED THIOPHENES
NISHIMURA, S
IMOTO, E
SAKUMOTO, A
NIPPON KAGAKU ZASSHI, 1961, 82 (11): : 1540 - &
[3] PHOTOOXYGENATION OF 2,3,5-TRISUBSTITUTED FURANS
APARICIO, FJL
DIAZ, RR
GARCIA, JI
CALVOFLORES, FG
BAUTISTA, FM
ANALES DE QUIMICA SERIE C-QUIMICA ORGANICA Y BIOQUIMICA, 1987, 83 (02): : 205 - 210
[4] Oxidative Trimerization of Amino Acids: Selective Synthesis of 2,3,5-Trisubstituted Pyridines
Xiang, Jia-Chen
Cheng, Yan
Wang, Zi-Xuan
Ma, Jin-Tian
Wang, Miao
Tang, Bo-Cheng
Wu, Yan-Dong
Wu, An-Xin
ORGANIC LETTERS, 2017, 19 (11) : 2997 - 3000
[5] Catalytic asymmetric hydrogenation of 2,3,5-trisubstituted pyrroles
Kuwano, Ryoichi
Kashiwabara, Manabu
Ohsumi, Masato
Kusano, Hiroki
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (03) : 808 - +
[6] Regioselective Synthesis of 2,3,4-or 2,3,5-Trisubstituted Pyrroles via [3,3] or [1,3] Rearrangements of O-Vinyl Oximes
Wang, Heng-Yen
Mueller, Daniel S.
Sachwani, Rachna M.
Kapadia, Rachel
Londino, Hannah N.
Anderson, Laura L.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09): : 3203 - 3221
[7] STRUCTURE OF 2,3,5-TRISUBSTITUTED 2-PYRROLIN-4-ONES
FREEMAN, JP
HADDADIN, MJ
TETRAHEDRON LETTERS, 1979, (50) : 4813 - 4816
[8] 5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via prins-type cyclization
Chavre, Satish N.
Choo, Hyunah
Cha, Joo Hwan
Pae, Ae Nim
Choi, Kyung Il
Cho, Yong Seo
ORGANIC LETTERS, 2006, 8 (16) : 3617 - 3619
[9] Emergence of 2,3,5-trisubstituted tetrahydrofuran natural products and their synthesis
Fernandes, Rodney A.
Gorve, Dnyaneshwar A.
Pathare, Ramdas S.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (36) : 7002 - 7025
[10] Solid-phase synthesis of 2,3,5-trisubstituted indoles
Wu, TYH
Ding, S
Gray, NS
Schultz, PG
ORGANIC LETTERS, 2001, 3 (24) : 3827 - 3830

← 1 2 3 4 5 →