Kinetics and mechanism of thermal gas-phase elimination of α- and β- (N-arylamino)propanoic acid: experimental and theoretical analysis

Al-Awadi, Sameera; Abdallah, Mariam R.; Hasan, Mohamad A.; Al‐Awadi, Nouria A.

doi:10.1016/j.tet.2004.01.087

Cited by 16 publications

(23 citation statements)

References 11 publications

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“…β-amino acid, was also not a leaving substituent. However, β-(Narylamino)propanoic acids reported to give ArNH 2 and acrylic acid [12] (reaction (3)) differ from the product formation of the β-amino carboxylic acid intermediates of the corresponding ethyl ester examined in the present work. These types of β-amino acids also decarboxylate by the same mechanism of α-amino acids.…”

Section: Ethyl Piperidine-3-carboxylatecontrasting

confidence: 63%

“…This result differs from the decarboxylation process of the α-amino acids described in reaction (1). In addition to this work, the pyrolysis products of 2-(N -arylamino)propanoic acids [12] were reported to be ArNH 2 , CH 3 CHO, and CO, which led to rationalize reaction pathway (2). In this work [12], the pyrolysis products of 3-(N -arylamino)propanoic acids were identified as ArNH 2 and acrylic acid.…”

Section: Introductionmentioning

confidence: 62%

“…In addition to this work, the pyrolysis products of 2-(N -arylamino)propanoic acids [12] were reported to be ArNH 2 , CH 3 CHO, and CO, which led to rationalize reaction pathway (2). In this work [12], the pyrolysis products of 3-(N -arylamino)propanoic acids were identified as ArNH 2 and acrylic acid. Further, both the experimental results and the theoretical calculations using an ab initio SCF method led to propose a mechanism of a four-membered cyclic transition state as shown in reaction (3).…”

Section: Introductionmentioning

confidence: 70%

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The elimination kinetics and mechanisms of ethyl piperidine‐3‐carboxylate, ethyl 1‐methylpiperidine‐3‐carboxylate, and ethyl 3‐(piperidin‐1‐yl)propionate in the gas phase

Monsalve

Rosas

Tosta

et al. 2005

Int J of Chemical Kinetics

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The gas-phase elimination kinetics of the above-mentioned compounds were determined in a static reaction system over the temperature range of 369-450.3• C and pressure range of 29-103.5 Torr. The reactions are homogeneous, unimolecular, and obey a first-order rate law. The rate coefficients are given by the following Arrhenius expressions: ethyl 3-(piperidin-1-yl) propionate, log k 1 (s −1 ) = (12.79 ± 0.16) − (199.7 ± 2.0) kJ mol −1 (2.303 RT) −1 ; ethyl 1-methylpiperidine-3-carboxylate, log k 1 (s −1 ) = (13.07 ± 0.12)-(212.8 ± 1.6) kJ mol −1 (2.303 RT) −1 ; ethyl piperidine-3-carboxylate, log k 1 (s −1 ) = (13.12 ± 0.13) − (210.4 ± 1.7) kJ mol −1 (2.303 RT) −1 ; and 3-piperidine carboxylic acid, log k 1 (s −1 ) = (14.24 ± 0.17) − (234.4 ± 2.2) kJ mol −1 (2.303 RT) −1 . The first step of decomposition of these esters is the formation of the corresponding carboxylic acids and ethylene through a concerted six-membered cyclic transition

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Section: Ethyl Piperidine-3-carboxylatecontrasting

confidence: 63%

Section: Introductionmentioning

confidence: 62%

Section: Introductionmentioning

confidence: 70%

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The elimination kinetics and mechanisms of ethyl piperidine‐3‐carboxylate, ethyl 1‐methylpiperidine‐3‐carboxylate, and ethyl 3‐(piperidin‐1‐yl)propionate in the gas phase

Monsalve

Rosas

Tosta

et al. 2005

Int J of Chemical Kinetics

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“…We have combined mechanistic and kinetic investigations to probe the gas-phase pyrolytic reaction in the synthesis of a wide rang of organic compounds. [5][6][7][8] In this work we wish to report further application of FVP in organic synthesis by describing a possible route for conversion of alkyl halides via their corresponding N-alkoxyphthalimides to functionally substituted aldehydes. The pyrolysates were qualitatively analyzed by HPLC, yields of each products was calculated by 1 H NMR (Table 1).…”

Section: Introductionmentioning

confidence: 99%

Gas-phase pyrolysis of N-alkoxyphthalimides to functionally substituted aldehydes: kinetic and mechanistic study

Al-Etaibi¹,

Al‐Awadi²,

Ibrahim³

et al. 2010

Arkivoc

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“…The following intermediates 16 and 17 may be formed by pericyclic reactions, followed by elimination of CO to give 18 [22]. Subsequent pericyclic reactions could lead to 19, which then undergoes rearrangement and aromatization via 20 to generate 4 and 21 (Scheme 3).…”

mentioning

confidence: 99%

A Novel One‐Pot Synthesis of Substituted Quinolines

Sabbaghan

Yavari

Hossaini

et al. 2010

Helvetica Chimica Acta

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A synthesis of quinoline derivatives is described via reaction between ethyl bromopyruvate (¼ ethyl 3-bromo-2-oxopropanoate), acetylenedicarboxylate, and isatin (¼ 1H-indole-2,3-dione) in the presence of NaH as a base. Also, these reactions were performed without ethyl bromopyruvate. The reaction in the presence of ethyl bromopyruvate provides regioselectively a quinoline with the ethyl ester group in 4-position. In the absence of ethyl bromopyruvate, the reaction leads to functionalized quinolines with the same ester groups in 2-, 3-, and 4-positions.Introduction. -Heterocyclic aromatic aza compounds, especially quinoline derivatives, are widely present in several natural compounds (e.g., Cinchona alkaloids) [1 -3] and pharmacologically active substances displaying a broad range of biological activity [4 -6]. Quinoline compounds have been found to possess antiasthmatic, antibacterial, anti-inflammatory, and antihypertensive properties [7 -9]. In addition to the medicinal applications, quinolines have been employed in the study of bioorganic and bioorganometallic processes [10]. Quinolines are also known for their formation of conjugated molecules and polymers that combine enhanced electronic, optoelectronic, or nonlinear optical properties with excellent mechanical properties [11]. A number of methods have been reported for the synthesis of quinolines involving a variety of metal catalysts and Lewis acids [12 -15]. Especially the Pfitzinger reaction [16] of isatins with a-methylidene carbonyl compounds is widely used for the synthesis of physiologically active derivatives of substituted quinoline-4-carboxylic acids [17]. However, many of these procedures are not fully satisfactory with regard to operational simplicity, cost of the reagent, drastic reaction conditions, and relatively low yield. Therefore, a simple, general, and efficient procedure is still in demand for the preparation of these important heterocyclic compounds.

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Kinetics and mechanism of thermal gas-phase elimination of α- and β- (N-arylamino)propanoic acid: experimental and theoretical analysis

Cited by 16 publications

References 11 publications

The elimination kinetics and mechanisms of ethyl piperidine‐3‐carboxylate, ethyl 1‐methylpiperidine‐3‐carboxylate, and ethyl 3‐(piperidin‐1‐yl)propionate in the gas phase

The elimination kinetics and mechanisms of ethyl piperidine‐3‐carboxylate, ethyl 1‐methylpiperidine‐3‐carboxylate, and ethyl 3‐(piperidin‐1‐yl)propionate in the gas phase

Gas-phase pyrolysis of N-alkoxyphthalimides to functionally substituted aldehydes: kinetic and mechanistic study

A Novel One‐Pot Synthesis of Substituted Quinolines

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