Regioselective Synthesis of Fluorescent Alkoxy-Substituted Phenazines and N-Alkyl Phenazinium Salts

被引：0

作者：

Reka, Pawel ^{[1
,2
]}

Ostrowska, Katarzyna ^{[1
]}

Grolik, Jaroslaw ^{[1
]}

Kotula, Olga ^{[1
]}

Urant, Grzegorz ^{[1
]}

Pikon, Maria ^{[1
]}

机构：

[1] Jagiellonian Univ, Fac Chem, Dept Organ Chem, PL-30387 Krakow, Poland

[2] Jagiellonian Univ Krakow, Doctoral Sch Exact & Nat Sci, PL-30348 Krakow, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 26期

关键词：

DERIVATIVES;

D O I：

10.1021/acs.joc.5c00923

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the regioselective synthesis of 2,3,7,8-tetraalkoxyphenazines and N-alkyl phenazinium salts was developed. The protocol allows the synthesis of compounds with up to four different substituents at the designed positions. The synthesis was achieved using nonsymmetrically substituted 4,5-dialkoxy-2-nitroanilines and 1-bromo-2-nitrobenzenes via Buchwald-Hartwig amination, followed by tandem catalytic reduction and oxidative cyclization. The synthesized derivatives exhibit intense fluorescence in solution, with significant changes in spectroscopic properties induced by solvent polarity, the presence of acids, and changing the counterion in N-alkyl phenazinium salts.

引用

页码：9118 / 9123

页数：6

共 25 条

[11] In situ synthesis of hexakis(alkoxy)diquinoxalino[2,3-a:2′,3′-c]phenazines:: Mesogenic phase transition of the electron-deficient discotic compounds [J].

Ong, CW ;

Liao, SC ;

Chang, TH ;

Hsu, HF .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3181-3185

[12] Total synthesis of maesanin and analogues [J].

Poigny, S ;

Guyot, M ;

Samadi, M .

TETRAHEDRON, 1998, 54 (49) :14791-14802

[13] Synthesis of Nonsymmetrically Substituted 2,3-Dialkoxyphenazine Derivatives and Preliminary Examination of Their Cytotoxicity [J].

Reka, Pawel ;

Grolik, Jaroslaw ;

Stadnicka, Katarzyna M. ;

Kolton-Wroz, Maria ;

Wolkow, Pawel .

JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (03) :1339-1351

[14] POTENTIAL ANTITUMOR AGENTS .51. SYNTHESIS AND ANTITUMOR-ACTIVITY OF SUBSTITUTED PHENAZINE-1-CARBOXAMIDES [J].

REWCASTLE, GW ;

DENNY, WA ;

BAGULEY, BC .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (05) :843-851

[15] Pheophorbide-phenazinium conjugate as a fluorescent light-up probe for G-quadruplex structure [J].

Ryazanova, Olga A. ;

Zozulya, Victor N. ;

Voloshin, Igor M. ;

Dubey, Larysa, V ;

Ilchenko, Mykola M. ;

Dubey, Igor Ya ;

Karachevtsev, Victor A. .

JOURNAL OF MOLECULAR STRUCTURE, 2020, 1214

[16]

Saito T., 2022, Patent No. [JP2022140101A, 2022191295]

[17] Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds [J].

Sheng, Jinyu ;

He, Ru ;

Xue, Jie ;

Wu, Chao ;

Qiao, Juan ;

Chen, Chao .

ORGANIC LETTERS, 2018, 20 (15) :4458-4461

[18]

Swan G. A., 1957, CHEM HETEROCYCLICCOM, V11

[19] Alchemy of donor-acceptor-donor multi-photofunctional organic materials: from construction of electron-deficient azaaromatics to exploration of functions [J].

Takeda, Youhei ;

Data, Przemyslaw ;

Minakata, Satoshi .

CHEMICAL COMMUNICATIONS, 2020, 56 (63) :8884-8894

[20] Efficient methods for the synthesis of 2-hydroxyphenazine based on the Pd-catalyzed N-arylation of aryl bromides [J].

Tietze, M ;

Iglesias, A ;

Merisor, E ;

Conrad, J ;

Klaiber, I ;

Beifuss, U .

ORGANIC LETTERS, 2005, 7 (08) :1549-1552

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