A convenient method for the synthesis of 2-trichloromethyl-4-p-substituted-phenyl-3h-1,5-benzodiazepines

Bonacorso, Hélio G.; Bittencourt, S. T.; Wastowski, Arci Dirceu; Wentz, Alexandre P.; Zanatta, Nilo; Marcos, Alicia; Martins, Marcos A. P.

doi:10.1016/s0040-4039(96)02145-4

Cited by 45 publications

(21 citation statements)

References 5 publications

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“…A convenient method to obtain a new series of 2-trichlorometyl-4-aryl-3//-l,5-benzodiazepines from the reaction of ß-aryl-ß-methoxyvinyl trichloromethyl ketones and o-phenylenediamine was previous reported [ 1 ]. Three independent molecules are found in the asymmetrc unit, differing by their confomations and the rotation of the CCI3 groups.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-trichloromethyl-4-phenyl-3H-1,5-benzodiazepine, C16H11Cl3N2

Lang

Bonacorso

Bittencourt

2000

Zeitschrift Für Kristallographie - New Crystal Structures

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CieHi 1CI3N2, monoclinic, P12,/nl (NO. 14), a =16.631(4) Ä, Source of materialTo a stirred solution of o-phenylenediamine (6 mmoles) in 4.0 ml of dry ethanol and 1 ml acetic acid, 4-methoxy-4-aryll,l,l-trichloro-3-buten-2-ones (6 mmoles) was added in small portions at 333 K. The solvent was removed and the crude solid product was recrystallized from methanol. DiscussionA convenient method to obtain a new series of 2-trichlorometyl-4-aryl-3//-l,5-benzodiazepines from the reaction of ß-aryl-ß-methoxyvinyl trichloromethyl ketones and o-phenylenediamine was previous reported [ 1 ]. Three independent molecules are found in the asymmetrc unit, differing by their confomations and the rotation of the CCI3 groups. One molecule adopts the conformation seen in the figure and th eother two represent a mirror image. The last milecules also show rotational disorder of the CCI3 group, which has been modeled giving approximately 0.9:0.1 occupancies over two split positions.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-trichloromethyl-4-phenyl-3H-1,5-benzodiazepine, C16H11Cl3N2

Lang

Bonacorso

Bittencourt

2000

Zeitschrift Für Kristallographie - New Crystal Structures

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“…In this case, only one isoxazoline and one 2-pyrazoline have been isolated. In particular, the synthetic potential of β-alkoxyvinyl trihalomethyl ketones to obtain series of novel heterocycles of five, 18 six, 19 seven membered rings 20 and more recently bisheterocyles 21 has been reported by us. Considering the biological importance of 2-pyrazolines and the fact that trichloromethylated analogs, such as, bisheteroaryl ketones are not yet known, it would be nice to demonstrate a new synthetic application of β-heteroaryl-β-methoxyvinyl trihalomethyl ketones.…”

Section: Introductionmentioning

confidence: 99%

Regiospecific synthesis of new non-condensed heteropolycyclic systems from beta-heteroaryl-beta-methoxyvinyl trihalomethyl ketones

Bonacorso¹,

Oliveira²,

Costa³

et al. 2005

J. Braz. Chem. Soc.

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isonicotinoil-hidrazinas (heteroarilhidrazidas), realizadas sob condições brandas e em meio alcoólico, forneceram em passo reacional único e regioespecificamente, uma série inédita composta por doze heteroaroil-2-pirazolinas trialometil heteroaril substituídas em rendimentos de 50-78%; um novo sistema heteropolicíclico não condensado.A novel series of twelve heteroaroyl-2-pyrazolines trihalomethyl and substituted heteroaryl, as non-condensed heteropolycyclic systems, have been synthesized in one-step in 50-78% yield from the regiospecific cyclocondensation reaction of 1,1,1-trifluoro(chloro)-4-methoxy-4-(2-furyl)-and 4-(2-thienyl)-3-buten-2-ones (β-alkoxyvinyl trihalometil ketones) with furoic hydrazide, 2-thiophenecarboxylic hydrazide and isonicotinic acid hydrazide (heteroaroylhydrazines) under mild conditions in methanol as solvent.Keywords: 2-pyrazolines, pyrazoles, 4-alkoxy-1,1,1-trihalo-alk-3-en-2-ones, hydrazides, heteroaroylhydrazines, hydrazines IntroductionAlthough many methods have been published for the synthesis of 1H-pyrazoles and their derivatives, attempts to perform the synthesis of a simple 4,5-dihydro-1H-pyrazoles (2-pyrazolines), has not yet been sucessfully achieved.1-3 By conventional procedure, pyrazoles have been obtained by directly reacting β-diketones with hydrazine.1 However, in most cases, 5-hydroxy-4,5-dihydro-1H-pyrazoles have been obtained when the N-1 atom is substituted with a strong electron-withdrawing group which stabilizes the -OH group and possibly hinders the elimination of the water molecule and the subsequent aromatization of the pyrazoline ring. 1Regarding pharmacological applications, 2-pyrazolines (4,5-dihydro-1H-pyrazoles) have been found to possess antitumor, 4 antibacterial, antifungal, antiviral, antiparasitic, antitubercular and insecticidal and others properties. [5][6][7][8][9][10][11][12][13][14][15][16] Some of these compounds also presented anti-inflammatory, anti-diabetic, anesthetic and analgesic properties. [13][14][15] For example, in a recent work Mamolo et al. 16 have synthesized a series of 5-aryl-1-isonicotinoyl-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazoles in a three-step in low yields, which involved an aldol condensation, cyclocondensation with hydrazine and N-acylation with isonicotinoyl chloride. These 2-pyrazolines showed an interesting antimycobacterial activity in vitro.In 2002, our research group reported 17 a new approach for the synthesis of a series of four ketones as 1,1,1-trifluoro(chloro)-4-methoxy-4-(2-furyl)-and 4-(2-thienyl)-3-buten-2-ones and their 4,4,4-trihalo-1-(2-heteroaryl)-1,3-butanediones derivatives. The autors also showed that mixtures of β-alkoxyvinyl trifluoromethyl ketones and the respective 1,3-butanediones derived from 2-acetylthiophene and 2-acetylfuran react with hydroxylamine hydrochloride, dry hydrazine and thiosemicarbazide hydrochloride leading to 3-(2-thienyl)-and 3-(2-furyl)azoles 869 Regiospecific Synthesis of New Non-Condensed Heteropolycyclic Systems Vol. 16, No. 4, 2005 derivatives. In this case, only one ...

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“…For example, trichloromethyl substituted benzodiazepines [2,3], 4,5-dihydro-pyrazoles [4], and quinazolines [5] have exhibited activity as acetylcholinesterase and ATPDase inhibitors [2], anxiolytics [3], antiinflammatories [4], analgesics [4], and cyclindependent kinases (CDKs) inhibitors [5] in the cell cycle proteins. Thus, the possibility to obtain trichloromethyl-substituted heterocycles [6][7][8] combined with the versatility of the trichloromethyl group as precursor of carboxyl groups [9][10][11], prompted us to devote special attention to the chemistry of the trichloromethyl-contained building blocks. Although many methods for the synthesis of thiazoles and pyrazoles have been reported [12][13][14][15][16][17][18], the synthesis of noncondensed 5,5-bicycles, as 2-(1H-pyrazol-1-yl)-thiazoles, was little explored.…”

Section: Introductionmentioning

confidence: 99%

“…This approach relies on the trichloroacetylation of enol ethers or acetals to give, in one step and good yields, ␤-alkoxyvinyl trichloromethyl ketones, which proved to be useful building blocks for the synthesis of five [7,[24][25][26][27], six [8,[28][29][30], and seven [9,31] membered trichloromethylated heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis and dehydration reaction of trichloromethylated 2‐(3‐phenyl‐5‐hydroxy‐4,5‐dihydro‐1H‐pyrazol‐1‐yl)‐4‐aryl‐5‐alkylthiazoles

Bonacorso

Muniz

Wastowski

et al. 2003

Heteroatom Chemistry

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A convenient method for the synthesis of 2-trichloromethyl-4-p-substituted-phenyl-3h-1,5-benzodiazepines

Cited by 45 publications

References 5 publications

Crystal structure of 2-trichloromethyl-4-phenyl-3H-1,5-benzodiazepine, C16H11Cl3N2

Crystal structure of 2-trichloromethyl-4-phenyl-3H-1,5-benzodiazepine, C16H11Cl3N2

Regiospecific synthesis of new non-condensed heteropolycyclic systems from beta-heteroaryl-beta-methoxyvinyl trihalomethyl ketones

Efficient synthesis and dehydration reaction of trichloromethylated 2‐(3‐phenyl‐5‐hydroxy‐4,5‐dihydro‐1H‐pyrazol‐1‐yl)‐4‐aryl‐5‐alkylthiazoles

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