Preparation of New 2-Amino- and 2,3-Diamino-pyridine Trifluoroacetyl Enamine Derivatives and Their Application to the Synthesis of Trifluoromethyl-containing 3H-Pyrido[2,3-b][1,4] diazepinols

被引：12

作者：

Bonacorso, Helio G. ^{[1
]}

Lourega, Rogerio V. ^{[1
]}

Righi, Fernando J. ^{[1
]}

Deon, Everton D. ^{[1
]}

Zanatta, Nilo ^{[1
]}

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

机构：

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

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 45卷 / 06期

关键词：

D O I：

10.1002/jhet.5570450619

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a novel series of the intermediates N(2)(N(3))-[1-alkyl(aryl/heteroaryl)-3-oxo-4,4,4-trifluoroalk-1-en-1-yl]-2-aminopyridines [F(3)CC(O)CH=CR(1)(2-NH-C(5)H(3)N)] and 2,3-diaminopyridines [F(3)CC(O)CH=CR(1)(2-NH(2)-3-NH-C(5)H(3)N)], where R(1) = H, Me, C(6)H(5), 4-FC(6)H(4), 4-ClC(6)H(4), 4-BrC(6)H(4), 4-CH(3)C(6)H(4), 4-OCH(3)C(6)H(4), 4,4'-biphenyl, 1-naphthyl, 2-thienyl, 2-furyl, is reported. The corresponding series of 2-aryl(heteroaryl)4-trifluoromethyl-3H-pyrido[2,3-b][1,4]diazepin-4-ols obtained from intramolecular cyclization reaction of the respective trifluoroacetyl enamines or from the direct cyclocondensation reaction of 4-methoxy-1,1,1-trifluoroalk-3-en-2-ones with 2,3-diaminopyridine, under mild conditions, is also reported.

引用

页码：1679 / 1686

页数：8

共 50 条

[41] Synthesis of novel thieno[2,3-b][1,6]naphthyridine and thieno [2′,3′: 2,3]pyrido[4,5-d]pyrimidine derivatives
Al-Omran, Fatima
El-Khair, Adel A.
JOURNAL OF CHEMICAL RESEARCH, 2007, (01) : 52 - 55
[42] Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones
A. S. Fisyuk
I. V. Kulakov
D. S. Goncharov
O. S. Nikitina
Y. P. Bogza
A. L. Shatsauskas
Chemistry of Heterocyclic Compounds, 2014, 50 : 217 - 224
[43] Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones
Fisyuk, A. S.
Kulakov, I. V.
Goncharov, D. S.
Nikitina, O. S.
Bogza, Y. P.
Shatsauskas, A. L.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (02) : 217 - 224
[44] Enantioselective synthesis of 2-and 3-substituted 2,3-dihydro[1,4]dioxino[2,3-b]pyridine derivatives and enantiomeric purity control by capillary electrophoresis
Lazar, S
Soukri, M
El Haddad, M
Akssira, M
Leger, JM
Jarry, C
Morin, PH
Guillaumet, G
CHIRALITY, 2005, 17 (01) : 30 - 36
[45] Synthesis of pyrido[2,3-b][1,4]benzoxazepines via a Friedel-Crafts cyclization
Guo, Sigen
Zhong, Xinran
Gong, Bowen
Cui, Hongming
Xiang, Jinbao
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (05) : 326 - 330
[46] Practicable synthesis of 1-(1-phenylethyl)-1H-pyrido[2,3-b][1,4]oxazine
Department of Chemistry, Changwon National University, Changwon, Gyeongnam 641-773, Korea, Republic of
不详
不详
Bull. Korean Chem. Soc., 2007, 12 (2486-2488):
[47] FUNCTIONAL DERIVATIVES OF THIOPHENE .4. NEW SYNTHESIS OF H-4-THIENO[2,3-B][1,4]-BENZOTHIAZINES
SHVEDOV, VI
ROMANOVA, OB
VASILEVA, VK
PAKHOMOV, VP
GRINEV, AN
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1973, (06): : 741 - 745
[48] Practicable synthesis of 1-(1-phenylethyl)-1H-pyrido[2,3-b][1,4]oxazine
Gim, Gyeonghyeon
Lijuan, Meng
Hua, Zuo
Ghate, Manjunath
Ahn, Chuljin
Won, Tae-Jin
Kim, Tae-Hyun
Reddy, Ch. Raji
Chandrasekhar, S.
Shin, Dong-Soo
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (12) : 2486 - 2488
[49] Synthesis and antiviral activity of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives
Bernardino, AMR
Pinheiro, LCS
Ferreira, VF
Azevedo, AR
Carneiro, JWD
Souza, TML
Frugulhetti, ICPP
HETEROCYCLIC COMMUNICATIONS, 2004, 10 (06) : 407 - 410
[50] Synthesis of 5-oxo-5H-[1]-benzopyrano[2,3-b]pyridine derivatives
Zheng, H
Lin, G
Weng, LL
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1998, 37 (09): : 933 - 935

← 1 2 3 4 5 →