Heterocyclic compounds from alloxan and amines. X. Amine purpurates

1970 ◽  
Vol 23 (2) ◽  
pp. 323 ◽  
Author(s):  
JW Clark-Lewis ◽  
K Moody
Keyword(s):  
Carbon Dioxide ◽  
Acetic Acid ◽  
Nitrogen Atom ◽  
Heterocyclic Compounds ◽  
Nitrogen Heterocycles ◽  
Heterocyclic Amine ◽  
Reaction Conditions

Secondary and tertiary alicyclic amines (piperidine, morpholine, N-ethyl-piperidine, and N-methylmorpholine), and aromatic nitrogen heterocycles (benzimidazole, 2-methyl- and 2-t-butyl-benzimidazole, and pyridine), are shown to yield the heterocyclic amine purpurates (murexide analogues) by reaction with anhydrous alloxan in dry acetic acid. The central nitrogen atom of the purpurate anion, normally derived from ammonia, is considered to arise from degradation of some of the alloxan, and is accompanied by liberation of carbon dioxide. Pyrrolidine did not yield a purpurate (or carbon dioxide) under the reaction conditions.

Iron-catalyzed radical cascade 6-endo cyclization of dienes towards fused nitrogen heterocycles initiated by an alkoxycarbonyl radical

2020 ◽  
Vol 18 (36) ◽  
pp. 7086-7089
Author(s):  
Shanshan Qiao ◽  
Peng-Cheng Qian ◽  
Fan Chen ◽  
Jiang Cheng
Keyword(s):  
Heterocyclic Compounds ◽  
Nitrogen Heterocycles ◽  
Reaction Conditions ◽  
Cascade Cyclization ◽  
Radical Cascade ◽  
Nitrogen Heterocyclic

An iron-catalyzed radical cascade cyclization of dienes initiated by an alkoxycarbonyl radical has been developed in the presence of (NH4)2S2O8, leading to a series of fused nitrogen heterocyclic compounds under relatively mild reaction conditions.

The chemistry of 4-(dicyanomethylene)-3-methyl-l-phenyl-2-pyrazoline-5- ones as a privileged scaffold in synthesis of heterocycles

2020 ◽  
Vol 17 ◽  
Author(s):  
Mohsen A.-M. Gomaa ◽  
Huda A. Ali
Keyword(s):  
Building Block ◽  
Heterocyclic Compounds ◽  
Recent Progress ◽  
Reaction Conditions ◽  
Azacrown Ethers ◽  
Wide Range ◽  
Privileged Scaffold ◽  
Number Of Publications ◽  
Near Future

Background : The reactivity of 4-(dicyanomethylene)-3-methyl-l-phenyl-2-pyrazoline-5-one DCNP 1 and its derivatives makes it valuable as a building block for the synthesis of heterocyclic compounds like pyrazolo-imidazoles, - thiazoles, spiropyridines, spiropyrroles, spiropyrans and others. As a number of publications have reported on the reactivity of DCNP and its derivatives, we compiled some features of this interesting molecule. Objective: This article aims to review the preparation of DCNP, its reactivity and application in heterocyclic and dyes synthesis. Conclusion: In this review we have provided an overview of recent progress in the chemistry of DCNP and its significance in synthesis of various classes of heterocyclic compounds and dyes. The unique reactivity of DCNP offers unprecedentedly mild reaction conditions for the generation of versatile cynomethylene dyes from a wide range of precursors including amines, α-aminocarboxylic acids, their esters, phenols, malononitriles and azacrown ethers. We anticipate that more innovative transformations involving DCNP will continue to emerge in the near future.

Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Metathesis Reaction ◽  
Synthetic Methodology ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Modular Synthesis

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

Study on the Synthesis of Isoamyl Acetate Catalyzed by Strong Acidic Cation Exchange Resin

2011 ◽  
Vol 396-398 ◽  
pp. 2411-2415 ◽  
Author(s):  
Ping Lan ◽  
Li Hong Lan ◽  
Tao Xie ◽  
An Ping Liao
Keyword(s):  
Acetic Acid ◽  
Reaction Time ◽  
Cation Exchanger ◽  
Cation Exchange Resin ◽  
Isoamyl Acetate ◽  
Molar Ratio ◽  
Esterification Reaction ◽  
Reaction Conditions ◽  
Optimum Reaction

Isoamyl acetate was synthesized from isoamylol and glacial acetic acid with strong acidic cation exchanger as catalyst. The effects of reaction conditions such as acid-alcohol ratio, reaction time, catalyst dosage to esterification reaction have been investigated and the optimum reaction conditions can be concluded as: the molar ratio of acetic acid to isoamylol 0.8:1, reaction time 2h, 25 % of catalyst (quality of acetic acid as benchmark). The conversion rate can reach up to 75.46%. The catalytic ability didn’t reduce significantly after reusing 10 times and the results showed that the catalyst exhibited preferably catalytic activity and reusability.

The Meisenheimer rearrangement in heterocyclic synthesis. II. Synthesis and X-ray crystal structure of a tetrahydro-1H-2,3-benzoxazocine and preparation of a hexahydro-2,3-benzoxazonine

1980 ◽  
Vol 33 (6) ◽  
pp. 1323 ◽  
Author(s):  
JB Bremner ◽  
EJ Browne ◽  
PE Davies ◽  
CLWAH Raston
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Acetic Acid ◽  
Crystal And Molecular Structure ◽  
Phosphorus Oxychloride ◽  
Crystallographic Analysis ◽  
Heterocyclic Synthesis ◽  
Reaction Conditions ◽  
X Ray ◽  
Heterocyclic Derivatives

The heterocyclic derivatives, 8,9-dimethoxy-3-methyl-1-phenyl-3,4,5,6- tetrahydro-1H-2,3-benzoxazocine(3a) and 9,10-dimethoxy-3-methyl-1- phenyl-1,3,4,5,6,7-hexahydro-2,3-benzoxazonine (3b),examples of two new ring systems, have been prepared by Meisenheimer rearrangement of the corresponding 2-benzazepine and 2-benzazocine N-oxide derivatives (2a) and (2b). The Bischler-Napieralski-type cyclization reaction was used in the preparation of the tertiary amine precursors of these N-oxides reaction conditions for the cyclization were critical and phosphorus oxychloride in refluxing butanenitrile was found to give the best yields of the seven- or eight-membered cyclic imine intermediates. Reductive cleavage of the benzoxazocine derivative (3a) with zinc in acetic acid followed by N-methylation gave the expected product, [2-{3- (dimethylamino)propyl}-4,5-di-methoxyphenyl]phenylmethanol (12). The crystal and molecular structure of (3a) has been determined by X-ray crystallographic analysis.

scholarly journals The Effect of NAA and BA on Carbon Dioxide Assimilation by Shoot Leaves of Spur-type `Delicious' and `Empire' Apple Trees

1997 ◽  
Vol 122 (6) ◽  
pp. 837-840 ◽  
Author(s):  
Matej Stopar ◽  
Brent L. Black ◽  
Martin J. Bukovac
Keyword(s):  
Carbon Dioxide ◽  
Acetic Acid ◽  
Gas Exchange ◽  
Malus Domestica ◽  
Assimilation Rate ◽  
Carbon Dioxide Assimilation ◽  
Gas Exchange Parameters ◽  
Apple Trees ◽  
Fruit Thinning ◽  
Exchange Parameters

The effects of NAA, BA, or Accel on CO2 assimilation of shoot leaves of mature bearing Redchief `Delicious' and `Empire' apple (Malus ×domestica Borkh.) trees were evaluated over two seasons. BA at 50 mg·L-1 did not significantly affect any of the gas-exchange parameters measured. NAA (15 mg·L-1) consistently suppressed CO2 assimilation rate (from ≈10% to 24% below that of the control). This suppression was NAA-concentration dependent, continued for >15 days after treatment, and was completely overcome in `Empire', but only partially or not at all in `Delicious' when BA was combined with NAA. These results are discussed in relation to fruit thinning and NAA-induced inhibition of fruit growth in spur-type `Delicious'. Chemical names used: 2-(1-napthyl) acetic acid (NAA); N-(phenyl)-1H-purine-6-amine (BA); BA + gibberellin A (GA)4+7 (Accel).

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