Convenient synthesis of 3-unsubstituted oxindole-1-carboxamides

被引：0

作者：

Porcs-Makkay, Marta ^{[1
]}

Volk, Balazs ^{[1
]}

Kokai, Eszter ^{[2
]}

Simig, Gyula ^{[1
]}

机构：

[1] EGIS Pharmaceut Plc, Div Chem Res, H-1475 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Fac Chem Engn, H-1521 Budapest, Hungary

来源：

TETRAHEDRON | 2012年 / 68卷 / 05期

关键词：

Oxindole; Amidation; Dephenoxycarbonylation; 4-N; N-Dimethylaminopyridinum; (DMAP); salt; DERIVATIVES;

D O I：

10.1016/j.tet.2011.12.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The multiple reactivity of the mesomeric anion formed by N- or C(3)-deprotonation of 3-unsubstituted oxindoles hampers the selective introduction of substituents onto the nitrogen atom. A conveniently applicable reaction sequence has been elaborated for the synthesis of 3-unsubstituted oxindole-1-carboxamides starting from the easily available 1,3-bis(phenoxycarbonyl)oxindoles. Selective amidation of the N-phenoxycarbonyl moiety and subsequent removal of the C(3)-phenoxycarbonyl moiety furnished the title compounds, which are useful building blocks for further functionalization. Besides the novel methodologies, several new representatives of this valuable compound family and their intermediates are also described below. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1427 / 1435

页数：9

共 50 条

[41] Convenient Synthesis of 3-Vinyl and 3-Styryl Coumarins
Gordo, Joana
Avo, Joao
Parola, A. Jorge
Lima, Joao C.
Pereira, Antonio
Branco, Paula S.
ORGANIC LETTERS, 2011, 13 (19) : 5112 - 5115
[42] Regioselective synthesis of 1-and 4-substituted 7-oxopyrazolo [1,5-a]pyrimidine-3-carboxamides
Drev, Miha
Groselj, Uros
Mevec, Spela
Pusavec, Eva
Strekelj, Janja
Golobic, Amalija
Dahmann, Georg
Stanovnik, Branko
Svete, Jurij
TETRAHEDRON, 2014, 70 (44) : 8267 - 8279
[43] Synthesis and anticholinesterase activity of coumarin-3-carboxamides bearing tryptamine moiety
Ghanei-Nasab, Samaneh
Khoobi, Mehdi
Hadizadeh, Farzin
Marjani, Azam
Moradi, Alireza
Nadri, Hamid
Emami, Saeed
Foroumadi, Alireza
Shafiee, Abbas
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 121 : 40 - 46
[44] Synthesis and Anticancer Evaluation of Novel 7-Aza-Coumarine-3-Carboxamides
Trifonov, Alexey V.
Gazizov, Almir S.
Tapalova, Anipa S.
Kibardina, Lyudmila K.
Appazov, Nurbol O.
Voloshina, Alexandra D.
Sapunova, Anastasiia S.
Luybina, Anna P.
Abyzbekova, Gulmira M.
Dobrynin, Alexey B.
Litvinov, Igor A.
Tauekel, Akerke K.
Yespenbetova, Sholpan O.
Burilov, Alexander R.
Pudovik, Michail A.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (12)
[45] Formal [4+2] Annulation of Oxindole-Embedded ortho-Quinone Methides with 1,3-Dicarbonyls: Synthesis of Spiro[Chromen-4,3'-Oxindole] Scaffolds
Shen, Yao-Bin
Li, Shuai-Shuai
Liu, Xicheng
Yu, Liping
Sun, Yun-Ming
Liu, Qing
Xiao, Jian
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07): : 3990 - 3999
[46] Synthesis and characterisation of novel N substituted 2-methylimidazo[1,2a]pyridine-3-carboxamides
Han, Tao
Shi, Zhichuan
Peng, Yongle
Zhao, Zhigang
JOURNAL OF CHEMICAL RESEARCH, 2011, (04) : 243 - 245
[47] CONVENIENT SYNTHESIS OF 1-(TRIMETHYLSILYL)- AND 1-(TRIMETHYLSTANNYL)VINYLPHOSPHONATES
Okada, Yoshiharu
Maruyama, Tomohiro
Tamura, Shin-ichi
Kameoka, Hirohito
Masuda, Satoshi
Tokuda, Yuichiro
Sakai, Junya
Nomura, Masato
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2014, 189 (06) : 778 - 790
[48] Alternative Approach to 1,2,4-Triazole-3-carboxamides
Ellis, David
SYNTHETIC COMMUNICATIONS, 2009, 39 (14) : 2585 - 2595
[49] Heterocyclization of thiocarbonohydrazides: Facile synthesis of 5-unsubstituted-1,3,4-thiadiazoles
Hassan, Alaa A.
Abdel-Latif, Fathy F.
Aziz, Mohamed Abdel
Mostafa, Sara M.
Braese, Stefan
Nieger, Martin
CHINESE CHEMICAL LETTERS, 2015, 26 (09) : 1183 - 1186
[50] Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates
Pruckova, Zdenka
Klasek, Antonin
Lycka, Antonin
Miksik, Ivan
Ruzicka, Ales
TETRAHEDRON, 2009, 65 (45) : 9103 - 9115

← 1 2 3 4 5 →