A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface

Balakrishna, Maravanji S.; Kaboudin, Babak

doi:10.1016/s0040-4039(00)02168-7

Cited by 182 publications

(79 citation statements)

References 17 publications

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“…Although the rearranged intermediates have not been directly detected in the EDTA decomposition, some potential fragments can still be proposed. It is reported that compound 1 could be prepared by condensation of o-PDA with 4-methyl-3-penten-2-one, 25 acetone, [26][27][28][29][30][31] acetonedicarboxylic acid, 32 or 2, 4, 4-trichloro-2-metylpentane 33 under different conditions ( Figure 5). These facts suggest that the rearranged intermediates might be one or some of these reactants.…”

Section: Resultsmentioning

confidence: 99%

“…[38][39][40][41][42] Several methods for preparing these compounds have been reported in the literature. [25][26][27][28][29][30][31][32] To our knowledge, the formation of the 1,5-benzodiazepine skeleton by the reaction of EDTA with o-PDA in strong acidic medium has not been reported so far. Although this reaction may not be an economic route for the preparation of compound 1, it helps us to sketch a new potential thermal decomposition mechanism for EDTA.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Thermal decomposition of ethylenediaminetetraacetic acid in the presence of 1,2-phenylenediamine and hydrochloric acid

Chen¹,

Gao²,

Wang³

2006

J. Braz. Chem. Soc.

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Considerando os produtos de reação do ácido etilenodiaminotetraacético (EDTA) com 1,2-fenilenodiamina (o-PDA), um novo processo para a decomposição térmica do EDTA é proposto. O meio ácido forte e a presença de o-PDA facilitam a decomposição de EDTA, como evidenciado pela temperatura relativamente baixa de reação. Em adição aos passos descritos na literatura, um processo de rearranjo está presente na reação de decomposição. Os intermediários rearranjados condensam com o-PDA, formando um inesperado composto biologicamente ativo 2,2,4-trimetil-3H-5-hidro-1,5-benzodiazepina, proporcionando a possibilidade de explorar um mecanismo de decomposição alternativo para este quelante amplamente utilizado.Based on the reaction products of ethylenediaminetetraacetic acid (EDTA) with 1,2-phenylenediamine (o-PDA), a novel thermal decomposition pathway of EDTA is proposed. The strong acidic medium and the presence of o-PDA facilitate the decomposition of EDTA as evidenced by the relatively lower reaction temperature. In addition to the steps described in literatures, rearrangement process is involved in the decomposition reaction. The rearranged intermediates condense with o-PDA, forming an unexpected biologically active compound 2,2,4-trimethyl-3H-5-hydro-1,5-benzodiazepine, thus provides the possibility to explore an alternative decomposition mechanism for this widely used chelator.Keywords: ethylenediaminetetraacetic acid, heterocycle, reaction mechanism, thermal decomposition, thermochemistry IntroductionEthylenediaminetetraacetic acid (EDTA) is one of the most extensively used chelating agents in chemistry, biochemistry, medicine, environmental sciences, and paper industry.1-6 As a scavenger for metal oxides or a stabilizer for metal ions, EDTA is also used at elevated temperatures to prevent scale deposits in high-pressure boilers or nuclear reactors owing to its thermal stability. Nevertheless, the behaviour of EDTA in waste water effluents 8,9 and natural aquatic systems 10 has incurred lots of threats to the natural environment. EDTA not only increases the total nitrogen contents, but also remobilizes most toxic heavy metals from solid matter into water solution and thus extends their biological life cycles. 11Hence, great attention has been paid to the study on decomposition mechanism 12-17 and treatment technique 18 for this aminopolycarboxylic acid complexing agent. Both EDTA and its disodium salt are stable to heat even at 423 K.19 EDTA begins to decompose at about 463 K and nearly 50% breaks down at 483 K in the presence of metal ions. 12 Stepwise decarboxylations and hydrolysis procedures of the ethylene C-N link of EDTA have been suggested by earlier researchers. 13,14 As shown in Figure 1, the decomposition mode may differ greatly with temperature changes. 14,15 Other factors such as acidity and reaction medium can also influence the decomposition of EDTA. For example, Vol. 17, No. 5, 2006 when ammonia was used as a reaction medium and reactant in a high pH system, both ammonolysis and hydrolysis of EDTA oc...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Thermal decomposition of ethylenediaminetetraacetic acid in the presence of 1,2-phenylenediamine and hydrochloric acid

Chen¹,

Gao²,

Wang³

2006

J. Braz. Chem. Soc.

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“…Owing to their versatile applications, various methods for the synthesis of benzodiazepines have been reported in the literature. These include condensation reactions of o-phenylenediamines with α,β-unsaturated carbonyl compounds [9] in the presence of various kind of catalysts [10][11][12][13][14][15][16][17][18] . The most extensively used methods for preparing 1,4-benzodiazepines begins with an 2-aminobenzophenone.…”

Section: Introductionmentioning

confidence: 99%

Two Step One-Pot Synthesis of Novel 5-(4-Fluorophenyl)-1H-Beno[e][1,4]Diazepin-2(3H)-One and it’s Base Catalyzed Transformation to N-Alkyl and C-3 Arylidene Derivatives

Patel

Khunt

Ghelani

et al. 2014

ILCPA

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“…Besides this, benzodiazepines are valuable synthons used for the preparation of fused ring compounds, such as triazolo (4), oxazino, or furanobenzodiazepine (5) have commercial uses in photography (6) (as dyes for acrylic fibres) and act as anti-inflammatory agents (7). The classical methods for the synthesis of benzodiazepines involves the condensation reaction of o-phenylenediamines with a,bunsaturated carbonyl compounds like b-haloketones (8,9) or ketones in the presence of a catalyst, such as BF 3 -etherate (10), NaBH 4 (11), polyphosphoric acid (12), MgO/POCl 3 (13), (OTf) 3 (14), Al 2 O 3 /P 2 O 5 (15), or HOAc under microwave (16) were employed for the transformation. Recent papers reported the use of other catalysts using stoichiometric amounts of zinc {(L) proline} (17), I 2 (18,19), ferric perchlorate (20), magnesium perchlorate (21) (25), and NBS (26) for the reaction.…”

Section: Introductionmentioning

confidence: 99%

Simple ammonium ionic liquid catalyses the 1,5-benzodiazepine derivatives under mild conditions

Attri

Pal

2010

Green Chemistry Letters and Reviews

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An incredibly elementary procedure for the effective synthesis of 1,5-benzodiazepine derivatives using triethyl ammonium acetate (TEAA) [Et 3 NH][CH 3 COO] ionic liquid has been developed. TEAA was found to be practical, inexpensive, reusable and has a simple work-up procedure, which is absent in other catalyst. The role of TEAA as the reaction medium as well as the catalyst has shown the benefits of the use of TEAA in organic synthesis. The effect of [Et 3 NH][CH 3 COO] on the synthesis of 1,5-benzodiazepine derivatives has been studied and results are provided herein.

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A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface

Cited by 182 publications

References 17 publications

Thermal decomposition of ethylenediaminetetraacetic acid in the presence of 1,2-phenylenediamine and hydrochloric acid

Thermal decomposition of ethylenediaminetetraacetic acid in the presence of 1,2-phenylenediamine and hydrochloric acid

Two Step One-Pot Synthesis of Novel 5-(4-Fluorophenyl)-1<i>H</i>-Beno[e][1,4]Diazepin-2(3<i>H</i>)-One and it’s Base Catalyzed Transformation to <i>N</i>-Alkyl and C-3 Arylidene Derivatives

Simple ammonium ionic liquid catalyses the 1,5-benzodiazepine derivatives under mild conditions

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