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

[31] New pyrrolo[ 1,2-b] pyridazine by 1,3-dipolar cycloaddition reactions
Dumitrascu, F.
Draghici, C.
Albulescu, A.
Dumitrescu, D.
REVISTA DE CHIMIE, 2006, 57 (08): : 866 - 869
[32] One-pot fluorination and Mannich reactions of 1,3-dicarbonyl compounds
Pham, Kenny
Huang, Xin
Zhang, Wei
TETRAHEDRON LETTERS, 2015, 56 (15) : 1998 - 2000
[33] One pot synthesis and reactions of novel 5-amino[1,3]thiazolo[3,2-b][1,2,4]triazoles
El-Sherief, Hassan A. H.
Hozien, Zeinab A.
El-Mahdy, Ahmed F. M.
Sarhan, Abdelwareth A. O.
ARKIVOC, 2011, : 71 - 84
[34] One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents
Xiao, Xiao
Hoye, Thomas R.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (25) : 9813 - 9818
[35] ONE-POT SYNTHESES OF 1H-PYRAZOLO[1,2-B]PHTHALAZINE-5,10-DIONES IN MOLTEN TBAB
Maheshwari, D. P. Loka
Hela, P. Gayatri
Satyanarayana, B.
HETEROCYCLIC LETTERS, 2020, 10 (01): : 39 - 45
[36] An efficient one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives
Ghahremanzadeh, Ramin
Shakibaei, Ghazaleh Imani
Bazgir, Ayoob
SYNLETT, 2008, (08) : 1129 - 1132
[37] Ferric Hydrogensulfate-Catalyzed One-Pot Synthesis of Indeno[1,2-b]quinoline-7-ones
Eshghi, Hossein
Nasseri, Mohammad Ali
Sandaroos, Reza
Molaei, Hamid Reza
Damavandi, Saman
SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2012, 42 (04) : 573 - 578
[38] MCM-41@CPTMS as an Efficient and High-Performance Catalyst for One-Pot Construction of Indeno[1,2-b]quinolin-8-one Derivatives
Najafi, Leila
Safaei-Ghomi, Javad
Oboudatian, Hourieh Sadat
CHEMISTRYSELECT, 2023, 8 (48):
[39] A Convenient One-Pot Synthesis of Thieno[2′,3′:4,5]Pyrimido[1,2-b]-[1,2,4,5]Tetrazines
Hassan, Allam A.
Khattab, Reham R.
Wasfy, Ashraf A. F.
Abuzeid, Khadiga M.
Hassan, Nasser A.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (04) : 907 - 912
[40] Concise copper-catalyzed one-pot tandem synthesis of benzimidazo[1,2-b]isoquinolin-11-one derivatives
Lu, Juyou
Gong, Xiaoyu
Yang, Haijun
Fu, Hua
CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4172 - 4174

← 1 2 3 4 5 →