Simple Synthesis of Fused Thiazolo[4,5-b]pyridines through Successive SNAr Processes

Synlett ◽  
2020 ◽  
Author(s):  
Alexey M. Starosotnikov ◽  
Maxim A. Bastrakov ◽  
Vadim V. Kachala ◽  
Ivan V. Fedyanin ◽  
Tatyana A. Klimova ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Chlorine Atom ◽  
Simple Synthesis ◽  
Smiles Rearrangement ◽  
One Pot

AbstractA convenient process is described for the synthesis of novel thiazolo[4,5-b]pyridines fused with triazole or pyrimidine rings. The base-promoted reactions of 2-chloro-3-nitropyridines with 1,3-(S,N)-binucleophiles (triazole-5-thiols, 4-oxopyrimidine-2-thiones) resulted in nucleophilic substitution of the chlorine atom and subsequent S–N-type Smiles rearrangement followed by nucleophilic substitution of the nitro group. Reactions with pyrimidine-2-thiones were carried out as one-pot processes while, in the case of triazole-5-thiols, isolation of intermediate substitution products was found to be preferable.

Simple Synthesis of Dimethyl Nitrobenzhydrylphosphonates and Heteroarylnitroarylacetonitriles via Vicarious Nucleophilic Substitution (VNS) Reaction

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 175-181
Author(s):  
Mieczysław Mąkosza ◽  
Małgorzata Bechcicka ◽  
Krzysztof Wojciechowski
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Nitro Compounds ◽  
Simple Synthesis ◽  
Para Position ◽  
Crucial Step ◽  
Vicarious Nucleophilic Substitution ◽  
Aromatic Nitro Compounds ◽  
Leaving Group ◽  
Aromatic Nitro

Acetals of dimethyl phenyl- and heteroaryl-α-hydroxymethanephosphonates were deprotonated to generate carbanions, which enter the vicarious nucleophilic substitution (VNS) of hydrogen in aromatic nitro compounds to form 4-nitrobenzhydrylphosphonates and α-heteroaryl-4-nitrobenzylphosphonates. Similarly acetals of cyano­hydrins of heteroaromatic aldehydes (furfural and 2-formylthiophene) react to form heteroaryl 4-nitroarylacetonitriles. The anion of the hemiacetal of acetaldehyde is an efficient leaving group in the base-induced β-elimination step – the crucial step in the VNS reaction. The reaction selectively occurred at the para-position to the nitro group.

The Synthesis of New Selenium-containing Heterocycles by the Oxidation Reaction of 2,4-Diaryltetrahydro-4H-selenochromenes

2020 ◽  
Vol 24 (15) ◽  
pp. 1663-1668
Author(s):  
Dmitriy Yurievich Direnko ◽  
Boris Ivanovich Drevko ◽  
Yaroslav Borisovich Drevko
Keyword(s):  
Nucleophilic Substitution ◽  
Chlorine Atom ◽  
Oxidation Reaction ◽  
Heterocyclic Fragment ◽  
Oxidative Aromatization

We have explored the reactions of tetrahydro-4H-selenochromenes in the presence of phosphoric pentachloride, and synthesized new condensate aroylbenzoselenophenes. During the reactions, tetrahydro-4H-selenochromenes with phosphoric pentachloride underwent oxidative aromatization and nucleophilic substitution for a chlorine atom of one of the protons in the alicyclic fragment. Also, the narrowing of the heterocyclic fragment occurred as in synthesized selenium-containing compounds earlier transformed into the corresponding condensate aroylbenzoselenophenes.

Vicarious nucleophilic amination of nitroquinolines with 4-amino-1,2,4-triazole

2008 ◽  
Vol 86 (7) ◽  
pp. 682-685 ◽  
Author(s):  
Barbara Szpakiewicz ◽  
Maria Grzegożek
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Para Position ◽  
Basic Medium ◽  
Ortho Position ◽  
Vicarious Nucleophilic Substitution

3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substitution (VNS), 4-amino-1,2,4-triazole.

scholarly journals The features of nucleophilic substitution of the nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazines

2017 ◽  
Vol 4 (1) ◽  
pp. 11-24
Author(s):  
E. N. Ulomsky ◽  
D. N. Lyapustin ◽  
V. V. Fedotov ◽  
O. S. El'tsov ◽  
I. M. Sapozhnikova ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group

scholarly journals A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 530-537 ◽  
Author(s):  
Moisés Romero-Ortega ◽  
Michelle Trujillo-Lagunas ◽  
Ignacio Medina-Mercado ◽  
Ivann Zaragoza-Galicia ◽  
Horacio Olivo
Keyword(s):  
Nucleophilic Substitution ◽  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles ◽  
Cyclization Reaction ◽  
Substitution Reactions ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Acyl Chlorides ◽  
Nucleophilic Substitution Reactions ◽  
One Pot Synthesis

A convenient two-step, one-pot synthesis of 4-chloro-2-(trichloromethyl)pyrimidines starting from 2-(trichloromethyl)-1,3-diazabutadienes is described. These nitrogen heterocycles were prepared by a sequential acylation/intramolecular cyclization reaction between 2-(trichloromethyl)-1,3-diazabutadienes and acyl chlorides in the presence of triethylamine followed by treatment with POCl3. This is the first report for the synthesis of this type of 4-chloro-2-(trichloromethyl)pyrimidine derivatives and serves as a source for a wide variety of other substituted pyrimidines by nucleophilic substitution reactions.

Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5H-Dibenzo[b,e][1,4]diazepin-11(10H)-ones

Synthesis ◽  
2020 ◽  
Author(s):  
Zbigniew Wróbel ◽  
Michał Tryniszewski ◽  
Robert Bujok ◽  
Roman Gańczarczyk
Keyword(s):  
Nitro Group ◽  
Carboxylic Acids ◽  
Carboxyl Group ◽  
Short Route ◽  
Step Method ◽  
One Pot ◽  
Aryl Group ◽  
Intramolecular Condensation ◽  
Reductive Condensation

Tributyl- or triphenylphosphine promotes a one-pot, three-step method for the synthesis of differently substituted dibenzodiazepinones from N-aryl-2-nitroanilines. Pyridine analogues and the corresponding thiazepinones can also be formed using this method. The process involves deoxygenation of the nitro group, then formation of an iminophosphorane intermediate and its intramolecular condensation with a carboxyl group placed in the N-aryl group. The role of the carboxyl group in the formation of the iminophosphorane and the mode of cyclization are discussed.

Nucleophilic substitution of the nitro group in 1-substituted 3-nitro-1H-1,2,4-triazoles in ethanolic potassium hydroxide

2020 ◽  
Vol 56 (8) ◽  
pp. 1100-1102
Author(s):  
Ani H. Hasratyan ◽  
Astkhik А. Sukoyan ◽  
Aleksan G. Shakhatuni ◽  
Gevorg G. Danagulyan ◽  
Hovhannes S. Attaryan
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Potassium Hydroxide

One-pot green and simple synthesis of actinian nickel-doped carbon nanoflowers for ultrasensitive sensing of quercetin

The Analyst ◽  
2019 ◽  
Vol 144 (24) ◽  
pp. 7283-7289 ◽  
Author(s):  
Yuan-Fei Gao ◽  
Xing Jin ◽  
Fen-Ying Kong ◽  
Zhong-Xia Wang ◽  
Wei Wang
Keyword(s):  
Hydrothermal Method ◽  
Simple Synthesis ◽  
One Pot ◽  
One Step

In this contribution, highly fluorescent actinian nickel-doped carbon nanoflowers were successfully synthesized by one-step traditional hydrothermal method and allowed the analysis of quercetin in a very facile method.

Microwave-Assisted, One-Pot Reaction of Pyridines, α-Bromoketones and Ammonium Acetate: An Efficient and Simple Synthesis of Imidazo[1,2-a]-pyridines

Synlett ◽  
2010 ◽  
Vol 2010 (11) ◽  
pp. 1606-1608 ◽  
Author(s):  
Mehdi Adib ◽  
Hamid Bijanzadeh ◽  
Ali Mohamadi ◽  
Ehsan Sheikhi ◽  
Samira Ansari
Keyword(s):  
Ammonium Acetate ◽  
Simple Synthesis ◽  
One Pot ◽  
Microwave Assisted
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