Aminomethylation of chlorophyll a derivatives using bis(N,N-dimethylamino)methane

2009 ◽  
Vol 13 (08n09) ◽  
pp. 949-956 ◽  
Author(s):  
Dmitri V. Belykh ◽  
Irina S. Tarabukina ◽  
Ivan V. Gruzdev ◽  
Mikhail I. Kodess ◽  
Aleksandr V. Kutchin
Keyword(s):  
Chlorophyll A ◽  
Weak Acid ◽  
Enol Form ◽  
Metal Free ◽  
Synthetic Procedure ◽  
Acrylic Derivative ◽  
High Yields ◽  
Vinyl Group ◽  
New Compounds

Bis(N,N-dimethylamino)methane has been shown to be a convenient reagent for the aminomethylation of chlorophyll a derivatives. Methylpheophorbide a (in enol form) and chlorin e 6 13-amides were aminomethylated with bis(N,N-dimethylamino)methane. Reactivity of methylpheophorbide a exo-ring and chlorin e 6 13-amides vinyl group were shown to be different. Selective methylpheophorbide a exo-ring aminomethylation was realized and isomerization of the exo-ring aminomethylation product with rhodochlorin 15-acrylic derivative formation was studied. The action of bis(N,N-dimethylamino)-methane in the presence of weak acid has been shown to be a simple and effective synthetic procedure to obtain a new chlorin e 6 derivative with two N,N-dimethylaminomethyl substituents in the vinyl group. The aminomethylation products' high yields, the simplicity of the procedure, the use of metal-free chlorines and the possible synthesis of new compounds, were found to be the main advantages of using bis(N,N-dimethylamino)methane as an aminomethylation reagent in chlorophyll a derivatives' chemistry.

Unsymmetrical phthalocyanines with cyclopalladated azo functions

2012 ◽  
Vol 16 (02) ◽  
pp. 192-199 ◽  
Author(s):  
H. Yasemin Yenilmez Akkurt ◽  
Ali ihsan Okur ◽  
Ahmet Gül
Keyword(s):  
Organic Solvents ◽  
Column Chromatography ◽  
Spectroscopic Analysis ◽  
Palladium Complex ◽  
Palladium Complexes ◽  
High Solubility ◽  
Synthetic Procedure ◽  
Different Types ◽  
New Compounds ◽  
Very High

In this study, a synthetic procedure for unsymmetrical metallophthalocyanines of the form M[Pc(AB3)], where A and B refer to two different types of peripheral functionality, has been developed and the new compounds have been converted to monomeric and dimeric palladium complexes. Asymmetrically substituted phthalocyanines were synthesized with the well-known statistical condensation method, by using two differently substituted precursors, namely 4-(2-ethoxyethoxy)-1-2-dicyanobenzene (1) and 4-{4-[Z/E]-phenylazo]-1-naphthyl}oxy-1,2-dicyanobenzene (2). Consequently, electron-donating 2-ethoxyethoxy groups and electron-withdrawing palladium complex are present in the same structure. Cyclopalladation was performed with [Pd(PhCN)2Cl2] to yield the bis-μ-chloro-bridged dimers and subsequently, the corresponding monomers were obtained by refluxing with three equivalents of potassium acetylacetonate. The resulting products were purified by column chromatography and characterized by several chemical and spectroscopic analysis methods. All compounds have very high solubility in organic solvents due to the presence of 2-ethoxyethoxy moiety.

Cinchona alkaloid and di-tert-butyldicarbonate–DMAP promoted efficient synthesis of (E)-nitroolefins

RSC Advances ◽  
2016 ◽  
Vol 6 (59) ◽  
pp. 54495-54502 ◽  
Author(s):  
Nataraj Poomathi ◽  
Paramasivan T. Perumal
Keyword(s):  
Cinchona Alkaloid ◽  
Efficient Synthesis ◽  
Metal Free ◽  
High Yields

A simple and efficient metal-free methodology for the synthesis of β-nitroolefins has been developed from arylidinemalononitrile using bifunctional cinchona alkaloid along with di-tert-butyldicarbonate–DMAP in high yields with total selectivity.

A metal-free hydrogenation of 3-substituted 2H-1,4-benzoxazines

2016 ◽  
Vol 14 (34) ◽  
pp. 8026-8029 ◽  
Author(s):  
Simin Wei ◽  
Xiangqing Feng ◽  
Haifeng Du
Keyword(s):  
Metal Free ◽  
High Yields

A metal-free hydrogenation of 3-substituted 2H-1,4-benzoxazines was realized to furnish the desired products in high yields with up to 42% ee.

Synthesis of functionalized 3-isochromanones via metal-free intramolecular alkoxylation-initiated cascade cyclization

2019 ◽  
Vol 21 (11) ◽  
pp. 3023-3028 ◽  
Author(s):  
Ying-Qi Zhang ◽  
Xin-Qi Zhu ◽  
Yin Xu ◽  
Hao-Zhen Bu ◽  
Jia-Le Wang ◽  
...  
Keyword(s):  
Allyl Ether ◽  
Metal Free ◽  
Cascade Cyclization ◽  
High Yields

A metal-free intramolecular alkoxylation-initiated cascade cyclization of allyl ether-tethered ynamides has been developed, leading to functionalized 3-isochromanones in high yields.

Synthesis, characterization and electrochemical properties of isoflavone substituted zinc(II), cobalt(II), and metal-free phthalocyanines

2019 ◽  
Vol 23 (07n08) ◽  
pp. 856-869 ◽  
Author(s):  
Efe B. Orman ◽  
Ahmet Arıbal ◽  
Ali R. Özkaya ◽  
Mustafa Bulut ◽  
Ümit Salan
Keyword(s):  
Tetrabutylammonium Perchlorate ◽  
Metal Free ◽  
Ft Ir ◽  
Electron Transfer Properties ◽  
New Compounds ◽  
Transfer Properties ◽  
Obvious Feature ◽  
Tof Ms ◽  
C Nmr

In this study, novel tetrasubstituted metallo- and metal-free phthalocyanines containing 7-hydroxy-4′-methoxyisoflavonoxy moieties at peripheral and non-peripheral positions have been prepared by cyclotetramerization of corresponding phthalonitriles. The most obvious feature of these quaternized complexes is their extensive solubility and non-aggregated species (especially non-peripherally substituted) in organic solvents such as chloroform, tetrahydrofuran, dimethylformamide and dimethylsulfoxide, which makes them candidates for use in many applications in different fields. The new compounds have been characterized by elemental analysis, FT-IR, UV-vis, 1H and [Formula: see text]C NMR and MS (Maldi-TOF MS). Voltammetric and in situ spectroelectrochemical measurements have been performed with the aim of characterizing the electron transfer properties of the compounds on Pt in dimethylsulfoxide/tetrabutylammonium perchlorate, compared to those of previously reported corresponding compounds with tetra 6-hydroxyflavonoxy substituents. The effect of aggregation on the redox character of these complexes was also discussed.

A Convenient Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Arylamidines via Chloramine-T Mediated Intramolecular Oxidative N–N Bond Formation

Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3883-3890
Author(s):  
Ashish Bhatt ◽  
Rajesh K. Singh ◽  
Ravi Kant ◽  
Bhupendra K. Sarma
Keyword(s):  
Reaction Time ◽  
Bond Formation ◽  
Available N ◽  
Short Reaction Time ◽  
Metal Free ◽  
Convenient Synthesis ◽  
Chloramine T ◽  
High Yields ◽  
Short Time

A convenient synthesis of 1,5-fused 1,2,4-triazoles from readily available N-arylamidines is reported. The reaction is efficiently promoted by chloramine-T to afford the desired products mostly in high yields and in relatively short time, through direct metal-free oxidative N−N bond formation. The mild nature of the synthesis and short reaction time are notable advantages of the developed protocol. This protocol is effective toward various substrates having different functionalities.

Metal-free switchable ortho/ipso-cyclization of N-aryl alkynamides: divergent synthesis of 3-selenyl quinolin-2-ones and azaspiro[4,5]trienones

2019 ◽  
Vol 17 (48) ◽  
pp. 10163-10166 ◽  
Author(s):  
Harekrishna Sahoo ◽  
Gowri Sankar Grandhi ◽  
Isai Ramakrishna ◽  
Mahiuddin Baidya
Keyword(s):  
Metal Free ◽  
High Yields

A selenium radical triggered switchable ortho/ipso-cyclization cascade of N-aryl alkynamides has been devised under metal-free conditions to access 3-selenyl quinolin-2-ones and 3-selenospiro[4,5]trienones in high yields (up to 98%).

A photo-auxiliary approach – enabling excited state classical phototransformations with metal free visible light irradiation

2017 ◽  
Vol 53 (10) ◽  
pp. 1692-1695 ◽  
Author(s):  
Akila Iyer ◽  
Steffen Jockusch ◽  
Jayaraman Sivaguru
Keyword(s):  
Excited State ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Uv Light ◽  
Light Irradiation ◽  
Metal Free ◽  
High Yields

To address the problem of using UV light to initiate traditional photoreactions, hydrazide based chromophores are evaluated as a “photo-auxiliary“ with visible light using a metal free photocatalyst to afford photoproducts in high yields.

Borane-catalyzed metal-free hydrogenation of 2,7-disubstituted 1,8-naphthyridines

2016 ◽  
Vol 14 (28) ◽  
pp. 6683-6686 ◽  
Author(s):  
Wei Wang ◽  
Xiangqing Feng ◽  
Haifeng Du
Keyword(s):  
Metal Free ◽  
High Yields

Metal-free hydrogenation of 2,7-disubstituted 1,8-naphthyridines was realized to furnish 1,2,3,4-tetrahydro-1,8-naphthyridines in high yields with up to 74% ee.

Metal free visible light driven oxidation of alcohols to carbonyl derivatives using 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst

RSC Advances ◽  
2015 ◽  
Vol 5 (102) ◽  
pp. 84328-84333 ◽  
Author(s):  
Suvendu Samanta ◽  
Papu Biswas
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Metal Free ◽  
Carbonyl Derivatives ◽  
Oxidation Of Alcohols ◽  
Visible Light Driven ◽  
High Yields

A metal-free transformation of alcohols to the corresponding carbonyls in high yields under visible-light irradiation has been achieved at room temperature using di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) as catalyst.

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