Construction of the cyclopenta[1,3]cyclopropa[1,2-b]naphthalene system in a one-pot domino reactions

被引：0

作者：

Krohn, K ^{[1
]}

Freund, C ^{[1
]}

Flörke, U ^{[1
]}

机构：

[1] Univ Gesamthsch Paderborn, Fachbereich Chem & Chem Tech, D-33098 Paderborn, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 1998卷 / 12期

关键词：

domino reactions; spirocyclization; Michael additions; beta-dicarbonyl compounds; nucleophilic substitution;

D O I：

10.1002/(SICI)1099-0690(199812)1998:12<2713::AID-EJOC2713>3.0.CO;2-G

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base treatment of the angucycline oligoketide precursor 6 unexpectedly afforded the spirocyclization product 7. An additional step in the domino cyclization process was observed starting from the quinoid bromo diketone 3b to yield stereospecifically the condensed tetracycle 8 with the benzo-annelated skeleton of the cubebol-type sesquiterpenes. The structure of 8 was confirmed by X-ray structure analysis. Further extension of the domino sequence by reaction of the dibromide 10 with acetonedicarboxylic eater II gave the cyclization/condensation products 12, 13, or 14, depending on the reaction conditions.

引用

页码：2713 / 2718

页数：6

共 50 条

[21] A 'one pot' synthesis of acenaphtho[1,2-b]benzo[f] and acenaphtho[1,2-b]benzo[h]quinolines.
Ray, JK
Kar, GK
Haldar, MK
SYNTHETIC COMMUNICATIONS, 1996, 26 (21) : 3959 - 3965
[22] One-pot domino reactions for synthesis of heterocyclic[3.3.3] propellanes and spiro[cyclopenta[b]pyridine-4,2′-indenes]
Zhang, Li-Juan
Yan, Chao-Guo
TETRAHEDRON, 2013, 69 (24) : 4915 - 4921
[23] ONE-POT SYNTHESES OF 4,8-DIALKYLBENZO[1,2-b:4,5-b']-DITHIOPHENES
Pappenfus, Ted M.
Seidenkranz, Daniel T.
Reinheimer, Eric W.
HETEROCYCLES, 2012, 85 (02) : 355 - 364
[24] A Novel and One-Pot Multicomponent Approach to the Synthesis of Dihyroindeno[1,2-b]pyrroles and Indeno[2′,1′:4,5]pyrrolo[1,2-a]-Fused 1,3-Diazaheterocycles
Alizadeh, Abdolali
Zarei, Ameneh
Rezvanian, Atieh
SYNTHESIS-STUTTGART, 2011, (03): : 497 - 501
[25] Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach
Demjen, Andras
Gyuris, Mario
Woelfling, Janos
Puskas, Laszlo G.
Kanizsai, Ivan
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 2338 - 2344
[26] A convenient one-pot synthesis and antimicrobial activity of pyrimido[1,2-b][1,2,4,5]tetrazines
Shawali, AS
Abdallah, MA
Zayed, MM
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (01) : 45 - 49
[27] A one-pot three-component approach to synthesis of novel dihydroxyoxoindeno[1,2-b]pyrrole derivatives
Rahimi, Fatemeh
Hosseini, Hajar
Bayat, Mohammad
TETRAHEDRON LETTERS, 2018, 59 (09) : 818 - 822
[28] One-Pot Domino Synthesis of 3-Amino-1,2-dihydroisoquinolines
Hamri, W.
Shyshkina, O. O.
Tarasiuk, T. M.
Volovnenko, T. A.
Mesbah, K.
Rhouati, S.
Volovenko, Y. M.
Medviediev, V. V.
Shishkin, O. V.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (05) : 1373 - 1376
[29] One-Pot Synthesis of Thiazolo[3,2-b](1,2,4)-triazoles
Wang, Dezhong
Zhang, Zhengqiang
Zhang, Lili
Shi, Haijian
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (07) : 1133 - 1137
[30] Simple synthesis of 7H-Phenaleno[1,2-b]furan-7-one derivatives by one-pot, three-component reactions
Teimouri, Mohammad Bagher
Mansouri, Farideh
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (04): : 507 - 510

← 1 2 3 4 5 →