Microwave-Assisted Synthesis of Fused and Substituted 2-Aminopyridines from β-Halo α,β-Unsaturated Aldehydes

被引：6

作者：

Gogoi, Junali ^{[1
]}

Gogoi, Pranjal ^{[1
]}

Goswami, Limi ^{[1
]}

Boruah, Romesh C. ^{[1
]}

机构：

[1] CSIR North East Inst Sci & Technol, Div Med Chem, Jorhat 785006, Assam, India

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 13期

关键词：

steroids; pyridines; enals; Knoevenagel reactions; cyclizations; ONE-POT SYNTHESIS; EFFICIENT METHOD; FACILE SYNTHESIS; INHIBITORS; PYRIDINES; DISCOVERY; PART;

D O I：

10.1055/s-0034-1380516

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aminopyridines were synthesized from -halo ,-unsaturated aldehydes by a microwave-assisted Knoevenagel reaction. The -halo-,-unsaturated aldehydes were, in turn, efficiently synthesized from the corresponding ketones by a Vilsmeier formylation reaction. The protocol was used to synthesize several novel steroidal and nonsteroidal fused 2-aminopyridine derivatives.

引用

页码：1905 / 1912

页数：8

共 43 条

[11] Microwave-assisted Pd-catalyzed synthesis of fused steroidal and non-steroidal pyrimidines from β-halo-α,β-unsaturated aldehydes
Gogoi, Junali
Gogoi, Pranjal
Bezbaruah, Pranjal
Boruah, Romesh C.
[J]. TETRAHEDRON LETTERS, 2013, 54 (52) : 7136 - 7139
[12] Synthesis of a novel class of steroidal tetrazolo[1,5-a]pyridines via intramolecular 1,3-dipolar cycloadditions
Gogoi, Junali
Bezbaruah, Pranjal
Saikia, Pallabi
Goswami, Jonalee
Gogoi, Pranjal
Boruah, Romesh Chandra
[J]. TETRAHEDRON LETTERS, 2012, 53 (12) : 1497 - 1500
[13] Ligand-Free Suzuki Cross-Coupling Reactions: Application to -Halo-,-Unsaturated Aldehydes
Gogoi, Pranjal
Bezboruah, Pranjal
Boruah, Romesh C.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) : 5032 - 5035
[14] Pyridine Group Assisted Addition of Diazo-Compounds to Imines in the 3-CC Reaction of 2-Aminopyridines, Aldehydes, and Diazo-Compounds
Gulevich, Anton V.
Helan, Victoria
Wink, Donald J.
Gevorgyan, Vladimir
[J]. ORGANIC LETTERS, 2013, 15 (04) : 956 - 959
[15] Substituted 2-aminopyridines as inhibitors of nitric oxide synthases
Hagmann, WH
Caldwell, CG
Chen, P
Durette, PL
Esser, CK
Lanza, TJ
Kopka, IE
Guthikonda, R
Shah, SK
MacCoss, M
Chabin, RM
Fletcher, D
Grant, SK
Green, BG
Humes, JL
Kelly, TM
Luell, S
Meurer, R
Moore, V
Pacholok, SG
Pavia, T
Williams, HR
Wong, KK
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (17) : 1975 - 1978
[16] De novo synthesis of substituted pyridines
Henry, GD
[J]. TETRAHEDRON, 2004, 60 (29) : 6043 - 6061
[17] Temperature-controlled synthesis of substituted pyridine derivatives via the [5C+1N] annulation of 1,1-bisalkylthio-1,4-pentanedienes and ammonium acetate
Hu, Jianglei
Zhang, Qian
Yuan, Hongjuan
Liu, Qun
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) : 2442 - 2445
[18] Structure-Based Design of 2-Aminopyridine Oxazolidinones as Potent and Selective Tankyrase Inhibitors
Huang, Hongbing
Guzman-Perez, Angel
Acquaviva, Lisa
Berry, Virginia
Bregman, Howard
Dovey, Jennifer
Gunaydin, Hakan
Huang, Xin
Huang, Liyue
Saffran, Doug
Serafino, Randy
Schneider, Steve
Wilson, Cindy
DiMauro, Erin F.
[J]. ACS MEDICINAL CHEMISTRY LETTERS, 2013, 4 (12): : 1218 - 1223
[19] Jones G., 1996, In comprehensive Heterocyclic Chemistry II, VVol.5, P167
[20] SYNTHESIS AND REACTIVITY OF 2,6-DIAMINO-4-METHYL-3-PYRIDINECARBONITRILE
KATRITZKY, AR
RACHWAL, S
SMITH, TP
STEEL, PJ
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) : 979 - 984

← 1 2 3 4 5 →