Synthesis of Quinolino[3′,4′:4,5] pyrrolo[1,2-f]phenanthridines by Regioselective Sonogashira Reaction Followed by Domino C-N Coupling/Hydroamination/C-H Arylation

被引：9

作者：

Ngo Nghia Pham ^{[1
,2
,3
]}

Salman, Ghazwan Ali ^{[1
,4
]}

Ponce, Marian Blanco ^{[1
]}

Tuan Thanh Dang ^{[1
,3
]}

Spannenberg, Anke ^{[2
]}

Ehlers, Peter ^{[1
,2
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, Albert Einstein Str 3A, D-18059 Rostock, Germany

[2] Univ Rostock eV, Leibniz Inst Katalyse, Albert Einstein Str 29A, D-18059 Rostock, Germany

[3] VNU Univ Sci Hanoi VNU HUS, Fac Chem, 19 Le Thanh Tong, Hanoi, Vietnam

[4] Univ Al Mustansiriyah, Coll Sci, Dept Chem, Palestine St, Baghdad, Iraq

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 26期

关键词：

Heterocycles; Palladium; Cyclization; Homogeneous catalysis; Domino reactions; COMPLEXES;

D O I：

10.1002/ejoc.201700371

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective and atom-economic synthesis of quinolino[3',4':4,5] pyrrolo[1,2-f] phenanthridines has been developed. The protocol involves a site-selective Sonogashira reaction of 3,4-dihaloquinoline, followed by a domino C-N coupling/hydroamination/C-H arylation reaction. Quinolino[3',4':4,5]pyrrolo[1,2-f] phenanthridines represent a hitherto unknown class of heterocyclic compounds.

引用

页码：3865 / 3873

页数：9

共 50 条

[21] The synthesis of novel polycyclic heterocyclic ring systems via photocyclization .19. Thieno[3',2':4,5]thieno[2,3-c]-naphtho[1,2-f]quinoline, thieno[3',2':4,5]thieno[2,3-c]naphtho[1,2-f][1,2,4]triazolo[4,3-a]quinoline and thieno[3',2':4,5]-thieno[2,3-c]naphtho[1,2-f]tetrazolo[1,5-a]quinoline
Luo, JK
Federspiel, RF
Castle, RN
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (05) : 1597 - 1601
[22] SYNTHESIS OF 4-H-AMINO-6 PYRROLO [1,2-A] THIENO [3,2-F] DIAZEPINE-1,4
RAULT, S
CUGNONDESEVRICOURT, M
ELKHASHEF, H
ROBBA, M
[J]. COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1980, 290 (09): : 169 - 171
[23] Synthesis of a new heterocyclic system, 5H-benz[4,5]imidazo[1,2-c]pyrazino [2′,3′:4,5]pyrrolo[3,2-e]pyrimidine [5]
Volovenko, Yu.M.
Dubinina, G.G.
[J]. Chemistry of Heterocyclic Compounds, 2000, 36 (11) : 1349 - 1350
[24] Palladium-Catalyzed Sonogashira-Coupling Conjoined C-H Activation: A Regioselective Tandem Strategy to Access Indolo- and Pyrrolo[1,2-a]quinolines
Shukla, Satya Prakash
Tiwari, Rakesh K.
Verma, Akhilesh K.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10382 - 10392
[25] Palladium-Catalyzed Regioselective C-H Arylation of 4-Azaindazole at C3, C5 and C7 Positions
Faarasse, Soukaina
El Kazzouli, Said
Bourzikat, Otmane
Bourg, Stephane
Aci-Seche, Samia
Bonnet, Pascal
Suzenet, Franck
Guillaumet, Gerald
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (16) : 3937 - 3945
[26] Synthesis of 5-Aryl-5H-pyrido[2',1':2,3]imidazo[4,5-b]indoles by Domino Pd- and Cu-Catalyzed C-N Coupling Reactions
Tran Quang Hung
Nguyen Minh Quan
Hoang Van Dong
Trinh Duy Nguyen
Hoang Le Tuan Anh
Trieu Quy Hung
Nguyen Van Tuyen
Ngo Thi Thuan
Tuan Thanh Dang
Langer, Peter
[J]. SYNLETT, 2019, 30 (03) : 303 - 306
[27] Synthesis of a new heterocyclic system 5H-benzo[4,5]imidazo[1,2-c]pyrazino[2′,3′:4,5]pyrrolo-[3,2-e]pyrimidine
Volovenko, YM
Dubinina, GG
[J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2000, (11): : 1564 - 1565
[28] Copper-mediated domino synthesis of pyrimido[4,5-b]carbazolones via Ullmann N-arylation and aerobic oxidative C-H amidation
Sreenivas, Devanga K.
Ramkumar, Nagarajan
Nagarajan, Rajagopal
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (17) : 3417 - 3423
[29] The synthesis of novel polycyclic heterocyclic ring systems via photocyclization.: 21.: Naphtho[2′,1′:4,5]thieno[2,3-c]naphtho[1,2-f]quinoline, naphtho[2′,1′:4,5]thieno[2,3-c]naphtho[1,2-f][1,2,4]triazolo[4,3-a]quinoline and naphtho[2′,1′:4,5]thieno[2,3-c]naphtho[1,2-f]-tetrazolo[1,5-a]quinoline
Luo, JK
Federspiel, RF
Castle, RN
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (01) : 171 - 174
[30] Well-Defined N-Heterocyclic Carbene-Palladium Complexes as Efficient Catalysts for Domino Sonogashira Coupling/Cyclization Reaction and C-H bond Arylation of Benzothiazole
Yadav, Seema
Singh, Ajeet
Mishra, Isha
Ray, Sriparna
Mobin, Shaikh M.
Dash, Chandrakanta
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (07)

← 1 2 3 4 5 →