2 edition of reactions of some heterocycles with dimethyl acetylenedicarboxylate. found in the catalog.
reactions of some heterocycles with dimethyl acetylenedicarboxylate.
Geoffrey Charles A. Bellinger
Thesis (Ph.D.) - University of East Anglia, School of Chemical Sciences, 1977.
Request PDF | New Heterocycles with Cycloamidine Substructure and Their Ringtransformation Reactions with Acetylenedicarboxylic Ester | The synthesis of pyrido[2,1-c]-1,2,4-triazines 6, pyrido[1,2. A novel reaction of 1,4-dipolar intermediate 3, generated from pyridine and dimethyl acetylenedicarboxylate, with aromatic aldehydes, resulted in the facile synthesis of 2-benzoylfumarates via the.
In the course of these optimization studies, l ‐proline (20 mol%) was also found to catalyze the reaction to furnish compound 33 in 50% yield within 30 min at room temperature from benzofuran‐2‐carbaldeh anil dimethyl acetylenedicarboxylate 32 and malononitrile 28 (Scheme 16). Some interesting nitrogen heterocycles, as well as other products, were synthesized by reactions of 2-cyano-N′-[(1,3-diphenyl-1H-pyrazolyl)methylidene]acetohydrazide with phenyl.
Heterocycles from the reaction of thione groups with acetylenic bonds. Advances in Heterocyclic Chemistry, – DOI: /b Triazoline 1, which is formally an α azoenamine, reacts with dimethyl acetylenedicarboxylate, acrylonitrile, methacrylonitrile, methyl methacrylate, phenylisocyanate, and sulfene to form products that appear to be derived from a common first step, the formation of a dipolar intermediate (e.g., 5).That intermediate may close to form either a 4-membered ring (6, 8) or ring-open to 7 with.
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The Reactions of some Heterocycles with Dimethyl Acetylenedicarboxylate. Author: Bellinger, G. ISNI: Awarding Body: University of East Anglia Current Institution: University of East Anglia Date of Award: Availability of Full Text.
Reactions of the sodium salts of some heterocyclic β-ketoesters with dimethyl acetylenedicarboxylate For reproduction of material from all other RSC journals and books: The sodium salts of several 1,2,3,4-tetrahydromethoxycarbonylbenzazepinones were treated with dimethyl acetylenedicarboxylate to give 1,2,3,6-tetrahydro Dimethyl acetylenedicarboxylate with indazole gave dimethyl indazolylfumarate and dimethyl α-indazolyl-β-indazolylsuccinate while the triazoles yielded similar but symmetrical succinates.
With diazoaminobenzene the corresponding fumarate and succinate, and dimethyl 2,3-dihydro,2-dimethoxycarbonylvinyl. Novel 2,5-dimethylenethiazolidinone derivatives have been prepared by reaction of malonthioamide derivatives with dimethyl acetylenedicarboxylate.
These compounds exist as separate (E,Z)- and. Treatment of indole with dimethyl acetylenedicarboxylate alone gave a mixture from which the major components tetramethyl carbazole-1,2,3,4-tetracarboxylate, tetramethyl 9-(-1,2-dimethoxycarbonylvinyl)-1,2-dihydrocarbazole-1,2,3,4-tetracarboxylate, trimethyl 5,6-dihydrooxophenanthridine-7,8,9-tricarboxylate andCited by: The article describes unusual [5 + 1]‐cyclocondensations of dimethyl acetylenedicarboxylate (DMAD), in which this reagent uncharacteristically acts as a 1,1‐biselelectrophilic agent.
Reactions of DMAD with 1,5‐bisnucleophilic 3‐(2‐aminophenyl)‐6‐R 1 ‐1,2,4‐triazin‐5(2H)‐ones yielded triazinoquinazoline‐derived diesters. Zhiyuan Chen, Qiuping Ding, Xingxin Yu and Jie Wu, Silver Triflate‐Catalyzed or Electrophile‐Mediated Tandem Reaction of N′‐(2‐Alkynylbenzylidene)hydrazides with Dimethyl Acetylenedicarboxylate, Advanced Synthesis & Catalysis,10, (), ().
Keywords: Thiosemicarbazone, dimethyl acetylene dicarboxylate, diethyl acetylene dicarboxylate, thiazoline Introduction Reaction of dimethyl acetylene dicarboxylate (DMAD) with esters and amides of dithiocarboxylic acids are well known methods for preparation of five membered S, and S,N-heterocycles1,2.
Thioureas possessing more than two N-H. New building blocks, 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides; Preparation and their Diels-Alder reaction with dimethyl acetylenedicarboxylate.
Tetrahedron51 (1), The reaction of 2-(phenylamino)- and 2-(dimethylamino)thiazoles with dimethyl acetylenedicarboxylate led unexpectedly to dimethyl 6-(phenylamino)- and 6-(dimethylamino)-3,4-pyridinedicarboxylates.
Those compounds reasonably result from a sequence of reactions initiated by a [2 + 2] cycloaddition of the alkyne to the formal CC of the thiazole ring. These pyridines were.
Dimethyl acetylenedicarboxylate in acetonitrile with pyridazine, 3-methylpyridazine, and 1-methylphthalazine gave pyrido[1,2-b]pyridazines, with smaller amounts of related pyrrolo[1,2-b]pyridazines.
3,6-Dimethylpyridazine, however, gave mostly an azepino[1,2-b]pyridazine. 2-Methyl- and 2,6-dimethyl-pyrazines gave only low yields of pyrrolo[1,2-a]pyrazines under these conditions. A Michael reaction occurs between 2-pyridone and dimethyl acetylenedicarboxylate, but 1-methylpyridone and the ester appear to give a Diels–Alder adduct which decomposes to -methylphthalimide.
Addition reactions of heterocyclic compounds. Part XXVII. 2-Pyridones with dimethyl acetylenedicarboxylate. The pronounced reactivity of nitrogen-containing heterocycles towards dimethyl acetylenedicarboxylate (DMAD) is well documented.
1., 1. (a), 1. (b) The reaction generally involves the initial addition of the N -heterocycle to DMAD to form a dipolar intermediate, which undergoes further reaction with DMAD leading to a variety of complex heterocyclic compounds; such reactions have.
A new series of heterocycles was synthesized via the reaction of readily obtainable 1,3‐diphenylpyrazole‐4‐carboxaldehyde thiosemicarbazone with many carbon electrophiles, for example, chloroacetic acid, chloroacetyl chloride, ethyl chloroacetate, dimethyl acetylenedicarboxylate, maleic anhydride, 3′‐nitro‐ω‐bromoacetophenone, malonic acid, acetylacetone, ethyl benzoylacetate.
Reactions of Dimethyl Acetylenedicarboxylate with 2,5-Dithiobiurea Derivatives Alaa A. Hassan* a Chemistry Department, Faculty of Science, Minia University, El-Minia, A.
Egypt Fax: +20(86) Email: [email protected] Synthesis of cyclazine and benzo[ g ]cyclazine derivatives by use of the [2 + 8] cycloaddition reaction of indolizines and dimethyl acetylenedicarboxylate.
Journal of Heterocyclic Chemistry26 (2), DOI: /jhet The reaction of dimethyl acetylenedicarboxylate with 1-methylvinylpyrrole is temperature dependent. At 80° the predominant reaction is the [4π + 2π] cycloaddition to give dimethyl 1-methyl-6,7-dihydroindole-4, 5-dicarboxylate, whereas at room temperature Michael addition of the acetylenic ester at the 5-position of the pyrrole ring to give fumaric and maleic ester derivatives also occurs.
The structure of the 2: 1 adduct of dimethyl acetylenedicarboxylate and 3-methyl(1-pyrrolidinyl)thiochromene has been determined by single-crystal X-ray diffraction. View Show abstract.
A novel three-component annulation reaction involving N-alkylimidazoles, dimethyl acetylenedicarboxylate, and in situ generated aryl methyl ketenes leading to the synthesis of 6-vinyl-1,3a-diazapentalene derivatives is reported. A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s).
Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose. Tetrahedron Letters No. 35, pp - Pergamon Press.
Printed in Great Britain. ELUCIDATION OF THE REACTIONS OF BENZOTHIAZOLE WITH DIMETHYL ACETYLENEDICARBOXYLATE Alexander McKillop* and Trevor S.B. Sayer School of Chemical Sciences, University of East Anglia Norwich NR4 7TJ, England (Received in France 20 February l9; .Novel Pyridine-Catalyzed Reaction of Dimethyl Acetylenedicarboxylate with Aldehydes: Formal [2 + 2] Cycloaddition Leading to 2-Oxobenzylidinesuccinates | Organic Letters.
The 1,4-zwitterionic intermediate generated from pyridine and DMAD adds to aldehydes in a formal [2 + 2] manner, resulting in the facile synthesis of 2-oxobenzylidinesuccinates.1. Introduction. Dimethyl acetylenedicarboxylate (DMAD) 1 is an electron-deficient alkyne diester in which the ester groups are conjugated with a carbon–carbon triple bond.
It is commonly used as a dienophile in cycloaddition reactions. It can also be used as a standard in Diels–Alder reactions to check the efficiency of various dienes.