Direct synthesis of Cbz-protected (2-amino)-6-(2-aminoethyl)pyridines

被引：5

作者：

Roy, Sudipta ^{[1
]}

Zych, Andrew J. ^{[1
]}

Herr, R. Jason ^{[1
]}

Cheng, Cliff ^{[2
]}

Shipps, Gerald W., Jr. ^{[2
]}

机构：

[1] AMRI, Dept Med Chem, Albany, NY 12212 USA

[2] Schering Plough Res Inst, Cambridge, MA 02141 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 11期

关键词：

2-(Aminoethyl)pyridines; Aminoethylation; Suzuki-Miyaura reactions; Pd-catalyzed reactions; 2-Halopyridines; HIV-1; REVERSE-TRANSCRIPTASE; ACTIVE HYDROGEN COMPOUNDS; CROSS-COUPLING REACTIONS; ASYMMETRIC-SYNTHESIS; NUCLEOPHILIC-SUBSTITUTION; DESIGN; SUZUKI; PYRIDYLETHYLATION; DERIVATIVES; INHIBITORS;

D O I：

10.1016/j.tet.2010.01.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel series of (2-amino)-6-(2-aminoethyl)pyridines were prepared by a convenient Suzuki-Miyaura coupling approach from 2-amino-6-bromopyridines. Benzyl vinylcarbamate was first treated with 9-BBN followed by aqueous NaOH and then the appropriate bromopyridine precursors were added into the mixture. The mixture was finally heated in presence of a palladium catalyst to provide the corresponding products in overall high yields. The procedure is extended to the preparation of related pyrazine and pyrimidine compounds as well as (2-amido)- and (2-alkoxy)-6-(2-aminoethyl)pyridines. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1973 / 1979

页数：7

共 50 条

[1] PHARMACOLOGICAL SYNTHESIS AND STUDY OF 6-(2-AMINOETHYL) BENZOXAZOLINONES
CAIGNARD, DH
COUQUELET, J
LESIEUR, D
LESPAGNOL, C
LAMAR, JC
BEAUGHARD, M
LEINOT, M
TISNEVERSAILLES, J
FARMACO-EDIZIONE SCIENTIFICA, 1985, 40 (11): : 854 - 868
[2] SYNTHESIS OF N-OMEGA AND OH PROTECTED 2[(2-AMINOETHYL)AMINO]ETHANOL
DZIEDUSZYCKA, M
MARTELLI, S
BOROWSKI, E
POLISH JOURNAL OF CHEMISTRY, 1995, 69 (04) : 632 - 634
[3] A solvent-free method for the direct synthesis of Cbz-protected β-amino ketones using triphenylphosphine dibromide
Buragohain, Pori
Saikia, Partha Pratim
Barua, Nabin C.
TETRAHEDRON LETTERS, 2013, 54 (27) : 3562 - 3564
[4] Synthesis and antiinflammatory activity of some 2-amino pyridines
Drabu, Sushma
Archna
Singh, Sukhjinder
Munirajam, S.
Kumar, Nitin
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 16 (04) : 411 - 412
[5] 2-ARYLQUINOLINE SYNTHESIS FROM Cbz-PROTECTED 2-AMINO-CHALCONE MEDIATED BY BF3•Et2O
Maegawa, Tomohiro
Nogata, Misa
Honda, Takaya
Nakamura, Akira
Miki, Yasuyoshi
HETEROCYCLES, 2017, 95 (01) : 608 - 614
[6] Convenient synthesis of Cbz-protected β-amino ketones by a copper-catalysed conjugate addition reaction
Wabnitz, TC
Spencer, JB
TETRAHEDRON LETTERS, 2002, 43 (21) : 3891 - 3894
[7] A Simple, Mild and Straight forward Route for the Synthesis of α-Ureidopeptidomimetics Using Cbz-Protected Amino Acid Esters
Ramachandra, Sagar N.
Srinivasulu, C.
Hosamani, Basavaprabhu
Santhosh, L.
Sureshbabu, Vommina V.
CHEMISTRYSELECT, 2018, 3 (43): : 12089 - 12092
[8] Direct synthesis of Cbz-protected β-amino ketones by iodine-catalyzed three-component condensation of aldehydes, ketones and benzyl carbamate
Phukan, Prodeep
Kataki, Dolly
Chakraborty, Pranita
TETRAHEDRON LETTERS, 2006, 47 (31) : 5523 - 5525
[9] SYNTHESES BASED ON VINYLPYRIDINES .7. SYNTHESIS OF 2-METHYL-5-(2-AMINOETHYL)-PYRIDINES
KOST, AN
VINOGRADOVA, EV
KOZLER, V
JOURNAL OF GENERAL CHEMISTRY USSR, 1963, 33 (11): : 3534 - &
[10] Synthesis of 2-aminoethyl glycosides of chitooligosaccharides
O. N. Yudina
Yu. E. Tsvetkov
N. E. Nifantiev
Russian Chemical Bulletin, 2015, 64 : 2932 - 2941

← 1 2 3 4 5 →