Synthesis of benzo[b]thieno[2,3-c]quinolines via palladium-catalyzed ring-closing reaction

被引：1

作者：

Gabor, Dora ^{[1
]}

Szabo, Timea ^{[1
]}

Keglevich, Gyorgy ^{[2
]}

Milen, Matyas ^{[1
]}

机构：

[1] Egis Pharmaceut Plc, Directorate Drug Subst Dev, POB 100, H-1475 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, POB 91, H-1521 Budapest, Hungary

来源：

TETRAHEDRON LETTERS | 2023年 / 115卷

关键词：

Bezothieno[2; 3-c]quinolines; Kabachnik-Fields reaction; Ring closure; Intramolecular arylation;

D O I：

10.1016/j.tetlet.2022.154298

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzo[b]thieno[2,3-c]quinolines were synthesized via Pd-catalyzed ring closure reaction of the a- aminophosphonates obtained by the Kabachnik-Fields condensation of benzo[b]thiophene-2-carbox-aldehydes, 2-iodoanilines and diethyl phosphite or dibenzyl phosphite. The intramolecular cyclizations remained incomplete under the conditions applied. The products were isolated in 11-42% yields, and the unreacted starting materials were recovered from the reaction mixture.(c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：6

共 50 条

[41] A new approach to the synthesis of functionalized pyrido[2,3-b]lindoles by way of a palladium-catalyzed ring closing reaction between the N-1 and C-9a positions
Abouabdellah, A
Dodd, RH
TETRAHEDRON LETTERS, 1998, 39 (15) : 2119 - 2122
[42] Total synthesis of octalactin A via ring-closing metathesis reaction
Buszek, KR
Sato, N
Jeong, Y
TETRAHEDRON LETTERS, 2002, 43 (02) : 181 - 184
[43] The synthesis of quinolines via denitrogenative palladium-catalyzed cascade reaction of o-aminocinnamonitriles with arylhydrazines
Xie, Jing
Huang, Hang
Xu, Tong
Li, Renhao
Chen, Jiuxi
Ye, Xueting
RSC ADVANCES, 2020, 10 (15) : 8586 - 8593
[44] Ring-closing metathesis as a key step to construct the 2,6-dihydropyrano[2,3-c]pyrazole ring system
Bieliauskas, Aurimas
Krikstolaityte, Sonata
Holzer, Wolfgang
Sackus, Algirdas
ARKIVOC, 2018, : 296 - 307
[45] THE SYNTHESIS OF NOVEL POLYCYCLIC HETEROCYCLIC RING-SYSTEMS VIA PHOTOCYCLIZATION .9. PHENANTHRO[9',10'/4,5]THIENO[2,3-C]QUINOLINE, BENZO[F]PHENANTHRO[9',10'/4,5]THIENO[2,3-C]QUINOLINE, AND BENZO[H]-PHENANTHRO[9',10'/4,5]THIENO[2,3-C]QUINOLINE
CAMOUTSIS, C
CASTLE, RN
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (01) : 153 - 156
[46] Synthesis and photochemical reaction of benzo[a]quinoxalino[2,3-c]phenazine dyes
Podsiadly, Radoslaw
Sokolowska, Jolanta
Kolinska, Jolanta
Grzelakowska, Aleksandra
COLORATION TECHNOLOGY, 2017, 133 (06) : 498 - 505
[47] Facile synthetic route to benzo[c]chromenones and thieno[2,3-c]chromenones
Shyyka, Olga Ya.
Martyak, Roman L.
Tupychak, Mykola A.
Pokhodylo, Nazariy T.
Obushak, Mykola D.
SYNTHETIC COMMUNICATIONS, 2017, 47 (24) : 2399 - 2405
[48] Three-Component Ring-Expansion Reaction of Indoles Leading to Synthesis of Pyrrolo[2,3-c]quinolines
Chen, Jinjin
Jiang, Shuxin
Shi, Weiliang
Jiang, Pingyu
Liu, Xinping
Huang, Huawen
Deng, Guo-Jun
ORGANIC LETTERS, 2023, 25 (37) : 6886 - 6890
[49] Novel synthesis of thieno[2,3-c]pyrazoles and thieno[2,3-d]pyrimidines
Ahluwalia, VK
Dahiya, A
Bala, M
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (07): : 715 - 717
[50] Substituted 3(2H)-Furanones by a Tandem Michael Addition/Palladium-Catalyzed Ring-Closing Protocol
John, Jubi
Hopf, Henning
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (05) : 841 - 845

← 1 2 3 4 5 →