Flexible BODIPY Platform That Offers an Unexpected Regioselective Heterocyclization Reaction toward Preparation of 2-Pyridone[a]-Fused BODIPYs

2019 ◽  
Vol 84 (4) ◽  
pp. 2133-2147 ◽  
Author(s):  
Natalia O. Didukh ◽  
Viktor P. Yakubovskyi ◽  
Yuriy V. Zatsikha ◽  
Gregory T. Rohde ◽  
Victor N. Nemykin ◽  
...  
Keyword(s):  
Heterocyclization Reaction

N-Methylated 1,8-Diaminonaphthalenes as Bifunctional Nucleo­philes in Reactions with α,ω-Dihalogenoalkanes: A Facile Route to Heterocyclic and Double Proton Sponges

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3427-3438
Author(s):  
Valery A. Ozeryanskii ◽  
Ekaterina V. Kolupaeva ◽  
Alexander F. Pozharskii
Keyword(s):  
Nitrogen Atom ◽  
Starting Material ◽  
One Pot ◽  
Heterocyclization Reaction ◽  
New Type ◽  
Organic Receptor ◽  
Proton Sponges ◽  
Short Time ◽  
First Time ◽  
Facile Route

The reaction of 1-dimethylamino-8-(methylamino)naphthalene with 1,3-dibromopropane chemoselectively leads to the product of N,N′-heterocyclization, while in the case of 1,4-dibromobutane and 1,2-bis(bromomethyl)benzene the process results in heterocyclization onto the same nitrogen atom with the formation of previously unknown 1-dimethylamino-8-pyrrolidino- and 1-dimethylamino-8-isoindolino-naphthalenes. The same reactions conducted without adding any auxiliary base lead to the formation of N,N′-linked double proton sponges as a new type of polynitrogen organic receptor. Proceeding as a sequence of quaternization–demethylation–cyclization steps, this heterocyclization process can also be used to construct six-membered rings (piperidino, morpholino), albeit in lower yields. The ability of 1,2-dibromoethane to brominate N-alkylated 1,8-diaminonaphthalenes is also described. It is shown for the first time that a commercially available 1,8-bis(dimethylamino)naphthalene (DMAN) can be used as a starting material in a heterocyclization reaction, which via a one-pot approach and in a short time can be converted into 1,5-dimethylnaphtho[1,8-bc]-1,5-diazacyclooctane or 1-dimethylamino-8-(pyrrolidin-1-yl)naphthalene.

Design, Synthesis, and Cytotoxicity of Indolizinoquinoxaline-5,12-dione Derivatives, Novel DNA Topoisomerase IB Inhibitors

2010 ◽  
Vol 63 (7) ◽  
pp. 1116 ◽  
Author(s):  
De-Qing Shen ◽  
Ning Wu ◽  
Yan-Ping Li ◽  
Zu-Ping Wu ◽  
Hong-Bin Zhang ◽  
...  
Keyword(s):  
Breast Carcinoma ◽  
Carcinoma Cell ◽  
Large Cell ◽  
Cancer Drug ◽  
Significant Activity ◽  
Dna Topoisomerase ◽  
Design Synthesis ◽  
Cell Lung Carcinoma ◽  
Heterocyclization Reaction ◽  
Topoisomerase Ib

A series of new indolizinoquinoxaline-5,12-dione derivatives were designed and synthesized via a heterocyclization reaction of 6,7-dichloroquinoxaline-5,8-dione with active methylene reagents and pyridine derivatives. The synthesized compounds exhibited significant activity to inhibit the growth of four human tumour cell lines, including lung adenocarcinoma cell, large-cell lung carcinoma cell, breast carcinoma cell, and ardriamycin-resistant breast carcinoma cell at micromolar range. These compounds were also investigated for their inhibition to DNA topoisomerase IB activity. The results indicated that the indolizinoquinoxaline-5,12-dione structure might be a potential pharmacophore in anti-cancer drug design.

ChemInform Abstract: Chemoselective Synthesis of 1-Substituted 4-Amino-2-(trifluoromethyl)-1H-pyrroles Through the Heterocyclization Reaction of 4-Methoxy-5-bromo-1,1,1-trifluoropent-3-en-2-ones with Amines.

ChemInform ◽  
2016 ◽  
Vol 47 (18) ◽  
Author(s):  
Estefania da C. Aquino ◽  
Guilherme Leonel ◽  
Vanessa C. Gariboti ◽  
Clarissa P. Frizzo ◽  
Marcos A. P. Martins ◽  
...  
Keyword(s):  
Heterocyclization Reaction ◽  
Chemoselective Synthesis

Heterocyclization Reaction ofα-Imino Carbonyl Compounds− Derivatives of 2,5-Dihydro-1H-imidazole Nitroxides

2003 ◽  
Vol 2003 (22) ◽  
pp. 4432-4437 ◽  
Author(s):  
Galina A. Roshchupkina ◽  
Natalie V. Pervukhina ◽  
Tatjana V. Rybalova ◽  
Yuri V. Gatilov ◽  
Alexey B. Burdukov ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Heterocyclization Reaction ◽  
Derivatives Of

Heterocyclization reaction of chloroacetylenephosphonates with 2-acylamidomalonates into 5-(dialkoxyphosphorylmethylidene)oxazolines

2012 ◽  
Vol 82 (4) ◽  
pp. 776-778 ◽  
Author(s):  
V. A. Khramchikhin ◽  
A. V. Dogadina ◽  
A. V. Khramchikhin ◽  
B. I. Ionin
Keyword(s):  
Heterocyclization Reaction

Straightforward synthesis of tri- and tetra-substituted 3-trifluoromethylfurans by heterocyclization reaction of perfluoroketene dithioacetals

Tetrahedron ◽  
2016 ◽  
Vol 72 (43) ◽  
pp. 6807-6814 ◽  
Author(s):  
Clément De Saint Jores ◽  
Ivan Mukan ◽  
Tatyana Yegorova ◽  
Dominique Harakat ◽  
Jean-Philippe Bouillon
Keyword(s):  
Heterocyclization Reaction
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