General Pathway for a Convenient One-Pot Synthesis of Trifluoromethyl-Containing 2-amino-7-alkyl(aryl/heteroaryl)-1,8-naphthyridines and Fused Cycloalkane Analogues

被引：12

作者：

Bonacorso, Helio G. ^{[1
]}

Andrighetto, Rosalia ^{[1
]}

Krueger, Nicolas ^{[1
]}

Zanatta, Nilo ^{[1
]}

Martins, Marcos A. P. ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Nucleo Quim Heterociclos NUQUIMHE, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

来源：

MOLECULES | 2011年 / 16卷 / 04期

关键词：

trifluoromethylated heterocyles; quinolines; naphthyridines; cycloalka[b][1,8]-naphthyridines; aminonaphthyridines; POTENTIAL ANTIHYPERTENSIVE AGENTS; 1,8-NAPHTHYRIDINE DERIVATIVES; REGIOSPECIFIC SYNTHESIS; ENOL ETHERS; CYCLIZATION; KETONES; DESIGN;

D O I：

10.3390/molecules16042817

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A convenient and general method for the synthesis in 26-73% yields of a new series of 7-alkyl(aryl/heteroaryl)-2-amino-5-trifluoromethyl-1,8-naphthyridines from direct cyclocondensation reactions of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones [CF3C(O)CH=C(R-1) OR, where R-1 = H, Me, Ph, 4-MePh, 4-OMePh, 4-FPh, 4-BrPh, 4-NO2Ph, 2-furyl, 2-thienyl and R = Me, Et] with 2,6-diaminopyridine (2,6-DAP), under mild conditions, is described. Another synthetic route also allowed the synthesis of 2-amino-5-trifluoromethyl-cycloalka[b][1,8]naphthyridines in 33-36% yields, from direct or indirect cyclocondensation reactions of five-, six-and seven-membered 2-trifluoroacetyl-1-methoxy-cycloalkenes with 2,6-DAP.

引用

页码：2817 / 2832

页数：16

共 25 条

[21] Preparation and characterization of the h-BN/Fe3O4/APTES-AMF/CuII nanocomposite as a new and efficient catalyst for the one-pot three-component synthesis of 2-amino-4-aryl(or heteroaryl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles
Rana, Pooja
Dixit, Ranjana
Sharma, Shivani
Dutta, Sriparna
Yadav, Sneha
Arora, Bhavya
Kaushik, Bhawna
Gawande, Manoj B. B.
Sharma, Rakesh K. K.
NANOSCALE, 2023, 15 (07) : 3482 - 3495
[22] Catalyst-free green synthesis of novel 2-amino-4-aryl-3-(4-fluorophenyl)-4,6,7,8-tetrahydroquinolin-5(1H)-ones via a one-pot four-component reaction under ultrasonic condition
Santhosh Govindaraju
Sumaiya Tabassum
Riyaz-ur-Rahaman Khan
Mohamed Afzal Pasha
Chemistry of Heterocyclic Compounds, 2016, 52 : 964 - 969
[23] Catalyst-free green synthesis of novel 2-amino-4-aryl-3-(4-fluorophenyl)-4,6,7,8-tetrahydroquinolin-5(1H)-ones via a one-pot four-component reaction under ultrasonic condition
Govindaraju, Santhosh
Tabassum, Sumaiya
Khan, Riyaz-ur-Rahaman
Pasha, Mohamed Afzal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (11) : 964 - 969
[24] 2-AMINO-4-ARYL-6-(OMEGA-CARBOXYALKYL)-5H-PYRROLO[3,4-D]PYRIMIDIN-7-(6H)ONES - PREPARATION VIA A ONE-POT SYNTHESIS OF 1-OMEGA-CARBOXYALKYL)-4-CARBETHOXY-2,3-DIOXOPYRROLIDINES
MADHAV, R
SNYDER, CA
SOUTHWICK, PL
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (06) : 1231 - 1235
[25] Application of PEG400 in the one-pot synthesis of 7-[4-alkyl- or (hetero)aryl-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridines via SNAr and Cu(I)-Catalyzed Azide-Alkyne Cycloaddition and preliminary evaluation of their anti-tumour activity
Rodrigues, Juliana M.
Calhelha, Ricardo C.
Ferreira, Isabel C. F. R.
Queiroz, Maria-Joao R. P.
TETRAHEDRON LETTERS, 2020, 61 (22)

← 1 2 3 →