Heterocyclic Synthesis With Azides. III. Reactions of Triazolines Made From Arylmethylidenemalonates

1994 ◽  
Vol 47 (7) ◽  
pp. 1375 ◽  
Author(s):  
RH Prager ◽  
P Razzino
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Azide ◽  
Trifluoroacetic Acid ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Heterocyclic Synthesis

Ethyl alkylidenemalonates reacted with sodium azide in dimethyl sulfoxide to give principally triazoles via the first-formed 4,5-dihydro-1H-1,2,3-tiriazoles. The triazolines themselves, and other compounds derived from them, were isolated in trace amounts. Ethyl alkylidenemalonates combined with benzyl azide in a 1,3-dipolar cycloaddition reaction to give 1-benzyl-4,5-dihydro-1H-1,2,3-triazoles. When treated with potassium t- butoxide in dimethyl sulfoxide , these adducts either aromatized to the corresponding triazoles, underwent deethoxycarbonylation but did not aromatize, or lost nitrogen to give ethyl benzylaminomethylidenemalonates. The proclivity for each of these three processes was determined by the C5 substituent of the 4,5-dihydro-1H-1,2,3-triazole. Treatment of the 1-benzyl-4,5-dihydro-1H-1,2,3-triazoles with trifluoroacetic acid gave ethyl diazomalonate.

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides

2016 ◽  
Vol 69 (1) ◽  
pp. 61 ◽  
Author(s):  
Rebecca E. Norman ◽  
Michael V. Perkins ◽  
Andris J. Liepa ◽  
Craig L. Francis
Keyword(s):  
Ethyl Acetate ◽  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Acid ◽  
Sulfonic Acid ◽  
Trifluoroacetic Anhydride ◽  
Ring Cleavage ◽  
Thermal Rearrangement ◽  
Heterocyclic Synthesis ◽  
Similar Treatment ◽  
Catalytic Hydrogenolysis

Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]triazines 5. Attempted catalytic hydrogenolysis of N7-benzyl pyrazolo[1,5-b][1,2,4,6]thiatriazines 2 in alcohols led to sulfamates 12 from thiatriazine ring cleavage. Ethyl acetate or tert-butanol as solvent allowed successful debenzylation to provide compounds 1. Aminolysis of compounds 2 gave sulfamides 13. Thermal rearrangement of compounds 2 afforded 6-benzyl-pyrazolo[3,4-e][1,2,4]thiadiazines 14.

Synthesis of 5-Aryloxazolidines via 1,3-Dipolar Cycloaddition Reaction of a Non-Stabilized Azomethine Ylide with Aromatic Aldehydes

2007 ◽  
Vol 60 (12) ◽  
pp. 898 ◽  
Author(s):  
John H. Ryan ◽  
Nadia Spiccia ◽  
Leon S.-M. Wong ◽  
Andrew B. Holmes
Keyword(s):  
Trifluoroacetic Acid ◽  
Cycloaddition Reaction ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition

The 1,3-dipolar cycloaddition reaction of a non-stabilized azomethine ylide 4a, formed in situ from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine 5 and a catalytic amount of trifluoroacetic acid, with aromatic aldehydes 3 gives rise to N-benzyl-5-aryloxazolidines 1. Under these conditions, 4-hydroxybenzaldehyde 3p undergoes two-fold addition of azomethine ylide 4a to afford bis adduct 11.

Heterocyclic Synthesis With Azides. I. The Reaction of Hydrazoic Acid With Ethoxymethylenemalonate

1992 ◽  
Vol 45 (10) ◽  
pp. 1571 ◽  
Author(s):  
A Donkor ◽  
RH Prager ◽  
MJ Thompson
Keyword(s):  
Sodium Azide ◽  
Trifluoroacetic Acid ◽  
Hydrazoic Acid ◽  
Heterocyclic Synthesis ◽  
Product Structures ◽  
Diethyl Ethoxymethylenemalonate

Reaction of diethyl ethoxymethylenemalonate with sodium azide in trifluoroacetic acid at 20� gives ethyl 5-ethoxyisoxazole-4-carboxylate (67%), diethyl cyanomalonate (21%) and diethyl ethoxyaminomethylenemalonate (5%). The last compound and its tautomer are converted into ethyl 1-ethoxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate. The product structures have been confirmed by synthesis or degradation.

scholarly journals New Polynuclear Nonfused Bis(1,3,4-Oxadiazole) Systems

2017 ◽  
Vol 58 (2) ◽  
Author(s):  
Yagoub Mansoori ◽  
Raana Sarvari
Keyword(s):  
Mass Spectroscopy ◽  
Elemental Analysis ◽  
Sodium Azide ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Acid Chlorides ◽  
Huisgen Reaction ◽  
C Nmr

In the present work, new polynuclear non-fused bis-(1,3,4-oxadiazole) compounds were obtained through Huisgen reaction of bis-(5-oxy-(1<em>H</em>)-tetrazoles with acid chlorides. Bis-tetrazole <strong>VIg</strong> was obtained from the 1,3-dipolar cycloaddition reaction between suberonitrile and sodium azide in DMF. The prepared compounds have been characterized by IR, <sup>13</sup>C NMR, mass spectroscopy and elemental analysis.

New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

Copper-catalyzed Convenient Synthesis and SAR Studies of Substituted-1,2,3-triazole as Antimicrobial Agents

2018 ◽  
Vol 16 (1) ◽  
pp. 3-10
Author(s):  
Aniket P. Sarkate ◽  
Kshipra S. Karnik ◽  
Pravin S. Wakte ◽  
Ajinkya P. Sarkate ◽  
Ashwini V. Izankar ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Triazole Derivatives ◽  
Sar Studies ◽  
Convenient Synthesis ◽  
Antibacterial And Antifungal

Background:A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent.Objective:We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity.Methods:A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively.Results and Conclusion:From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.

Rapid Access to Novel 1,2,3-Triazolo-Heterocyclic Scaffolds via Tandem Knoevenagel Condensation/Azide–Alkyne 1,3-Dipolar Cycloaddition Reaction in One Pot

2014 ◽  
Vol 16 (9) ◽  
pp. 466-477 ◽  
Author(s):  
Ram Awatar Maurya ◽  
Praveen Reddy Adiyala ◽  
D. Chandrasekhar ◽  
Chada Narsimha Reddy ◽  
Jeevak Sopanrao Kapure ◽  
...  
Keyword(s):  
Knoevenagel Condensation ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Rapid Access

One pot synthesis of novel dispiro[oxindole-thiazolidinedione/thioxo-thiazolidinone/dihydro pyrazolone]-pyrrolidines via 1,3-dipolar cycloaddition reaction of azomethine ylides

2006 ◽  
Vol 43 (6) ◽  
pp. 1635-1640 ◽  
Author(s):  
Shashikanth Ponnala ◽  
Devi Prasad Sahu ◽  
Rishi Kumar ◽  
Prakas R. Maulik
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
One Pot Synthesis

Synthesis of novel isoxazole-benzoquinone hybrids via 1,3-dipolar cycloaddition reaction as key step

2012 ◽  
Vol 53 (32) ◽  
pp. 4108-4113 ◽  
Author(s):  
P. Ravi Kumar ◽  
Manoranjan Behera ◽  
K. Raghavulu ◽  
A. Jaya Shree ◽  
Satyanarayana Yennam
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition

ChemInform Abstract: Facile Synthesis of β-Lactam-Grafted Spirooxindolopyrrolidine Through Regioselective 1,3-Dipolar Cycloaddition Reaction.

ChemInform ◽  
2012 ◽  
Vol 43 (29) ◽  
pp. no-no
Author(s):  
Natarajan Arumugam ◽  
Raghavachary Raghunathan
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Facile Synthesis
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