Synthesis and Reactions of Some New 3-Amino-2-substituted Thieno[2,3-b]quinolines

1992 ◽  
Vol 57 (11) ◽  
pp. 2359-2366 ◽  
Author(s):  
Etify Abdel-Ghafar Bakhite
Keyword(s):  
Acetic Anhydride ◽  
Carbon Disulfide ◽  
Nitrous Acid ◽  
Aromatic Amines ◽  
Triethyl Orthoformate ◽  
Ethyl Iodide ◽  
Polycyclic Compounds

Reaction of 3-cyano-quinolin-2(1H)-thione (II) with ω-bromoacetophenones gave 3-amino-2-aroyl-thieno[2,3-b]quinolines (IVa-IVd). Whereas, interaction of II with chloroacetanilides yielded the corresponding thioesters Va-Vc which cyclized into 3-amino-2-arylcarbamoylthiene[2,3-b]quinolines (VIa-VIc) on treatment with ethoxide. Compounds VIa-VIc were reacted with nitrous acid, triethyl orthoformate and carbon disulfide to afford the fused polycyclic compounds VIIa-VIIc, VIIIa-VIIIc and IXa-IXc, respectively. Also treatment of IXa-IXc with ethyl iodide gave 3-ethylthio derivatives Xa-Xc. Moreover, refluxing of VIa-VIc with acetic anhydride resulted in the formation of oxazinone XI which recyclized into pyrimidinones XIIIa-XIIIc upon reaction with aromatic amines.

Synthesis of 3-benzylxanthine and Lumazine Analogues

2005 ◽  
Vol 2005 (4) ◽  
pp. 262-266 ◽  
Author(s):  
El Sayed H. El Ashry ◽  
Shaker Youssif ◽  
Maged El Ahwany ◽  
Mohamed El Sanan
Keyword(s):  
Acetic Anhydride ◽  
Carbon Disulfide ◽  
Nitrous Acid ◽  
Acid Treatment ◽  
Aromatic Aldehydes ◽  
Diethyl Oxalate

Several xanthines (7–13) are prepared by the cyclisation of 1-benzyl-5,6-diaminouracil with single-carbon inserting agents such as aromatic aldehydes, formamides, acetic anhydride, carbon disulfide, and nitrous acid. Treatment of 6-amino-1-benzyl-5-nitrosouracil with anilinobenzylidene derivatives (14–18) affords 7-hydroxyxanthines (19–23). Cyclisation of the diaminouracil 3 with glyoxal, benzil, and diethyl oxalate leads to lumazines (25–28).

scholarly journals Synthesis of some pyrazolo[3,4-d]pyrimidines and their fused triazole and tetrazole derivatives

1999 ◽  
Vol 64 (11) ◽  
pp. 655-662 ◽  
Author(s):  
Samira Swelam ◽  
Abd El-Salam ◽  
Magdi Zaki
Keyword(s):  
Acetic Anhydride ◽  
Formic Acid ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Nitrous Acid ◽  
Reaction Medium ◽  
Pyrimidine Derivatives ◽  
Elemental Analyses ◽  
Tetrazole Derivatives

Reaction of 2 with different reagents, namely formic acid, acetic anhydride and trichloroacetonitrile, yielded pyrazolo[3,4-d]pyrimidine derivatives 3, 5 and 6, respectively. Pyrazolo[3,4-d]pyrimidine m-thiazine(7) and 2,4-(1H,3H)dithione (8) derivatives were formed by the action of carbon disulfide on 2, depending on the reaction medium. Interaction of 7 with hydrazine hydrate yielded the aminoimino derivative 9 which reacted with acetic anhydride, triethyl orthoacetate and/or appropriate aldehydes to give 11, 12 and 13a,b, respectively. Methylation of compound 8 gave 14, which reacted with hydrazine hydrate to afford the monohydrazino derivative 15. Reaction of 15, with formic acid and nitrous acid afforded pyrazolo[4,3-e]triazolo[1,5-c]pyrimidine (16) and pyrazolo[4,3-e]tetrazolo-[1,5-c]pyrimidine (17) derivatives, respectively. The structures of products 3-17 were identified in light of their elemental analyses and spectra data.

scholarly journals Green synthesis of new lawsone enaminones and their Z/E(CC)-isomerization induced by organic solvent

RSC Advances ◽  
2021 ◽  
Vol 11 (21) ◽  
pp. 12990-12994
Author(s):  
Abolfazl Olyaei ◽  
Amir Mohamadi ◽  
Nilufar Rahmani
Keyword(s):  
Organic Solvent ◽  
Green Synthesis ◽  
Aromatic Amines ◽  
Solvent Free ◽  
Triethyl Orthoformate ◽  
Guanidinium Chloride ◽  
New Class ◽  
Solvent Free Conditions

The synthesis of a new class of lawsone enaminone derivatives by using lawsone, triethyl orthoformate and aromatic amines in the presence of guanidinium chloride under solvent-free conditions has been developed.

Isopropyl N-Arylmalonamates. Synthesis, Structure, Conformation and Reactions with Carbon Disulfide

2006 ◽  
Vol 71 (1) ◽  
pp. 59-76 ◽  
Author(s):  
Wolf-Dieter Rudorf ◽  
Dušan Loos ◽  
Joanna Wybraniec ◽  
Naďa Prónayová ◽  
Ryszard Gawinecki ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonding ◽  
Carbon Disulfide ◽  
Aromatic Amines ◽  
Alkylating Agent ◽  
Sodium Hydride ◽  
Open Chain ◽  
Ketene Dithioacetals ◽  
Correlation Analyses ◽  
C Nmr

Acylation of aromatic amines 1 with diisopropyl malonate (2) leads to a mixture of isopropyl N-arylmalonamates 3 and malonanilides 4. The reaction of 3 with carbon disulfide in the presence of sodium hydride gives disodium salts 5. Treatment of 5 with an alkylating agent yields the open-chain or cyclic ketene dithioacetals 6, 7 or 8. The molecular structure, hydrogen bonding and preferential conformation of the isopropyl N-arylmalonamates 3, 6 and 7 were investigated using correlation analyses of IR, 13C NMR and AM1 semiempirical data.

Properties relating to critical phenomena in the acetic anhydride – acetone – carbon disulfide system

1970 ◽  
Vol 48 (6) ◽  
pp. 904-909 ◽  
Author(s):  
A. N. Campbell ◽  
E. M. Kartzmark
Keyword(s):  
Acetic Anhydride ◽  
Carbon Disulfide ◽  
General Rule ◽  
Dielectric Constants ◽  
Excess Volumes ◽  
Solution Temperature ◽  
Critical Solution Temperature ◽  
Heats Of Mixing ◽  
Upper Critical Solution Temperature ◽  
Molar Polarization

The following physical properties of the acetic anhydride – acetone – carbon disulfide system have been investigated: congruent compositions, excess volumes, dielectric constants. For the system acetone – carbon disulfide, the excess volumes and the molar polarizations are much greater than those required by the mixture rule. From this we deduced that this system is very non-ideal and might, at a suitable temperature, form two layers; two liquid layers did indeed form at −73 °C, the upper critical solution temperature occurring somewhere between this temperature and 0 °C. We offer it as a general rule that, if the deviation from additivity of molar polarization is large and positive, two layers will form at a sufficiently low temperature, provided that solid phases do not intervene. This deduction becomes almost a certainty if large positive deviations from additivity of molar volume and large positive heats of mixing are also present.

Cyanoacetylation of Indoles, Pyrroles and Aromatic Amines with the Combination Cyanoacetic Acid and Acetic Anhydride

Synthesis ◽  
2004 ◽  
Vol 2004 (16) ◽  
pp. 2760-2765 ◽  
Author(s):  
Jan Bergman ◽  
Johnny Slätt ◽  
Ivan Romero
Keyword(s):  
Acetic Anhydride ◽  
Aromatic Amines ◽  
Cyanoacetic Acid

scholarly journals Synthesis n-oxides of pyridylacethylene amines based on 2-methyl-5-ethynylpyridine

2021 ◽  
pp. 48-53
Keyword(s):  
Reaction Time ◽  
Acetic Anhydride ◽  
Mannich Reaction ◽  
Aromatic Amines ◽  
Pmr Spectroscopy ◽  
The Mannich Reaction

The aim of this work is to study the reaction of 2-methyl-5-ethynylpyridine N-oxide with some aliphatic and aromatic amines to obtain N-oxides of pyridylacetylenic amines. 2-Methyl-5-ethylpyridine converted to 2-methyl-5-vinylpyridine by dehydrogenation, and 2-methyl-5-ethynylpyridine obtained by bromination and dehydrobromination. 2-methyl-5-ethynylpyridine N-oxide synthesized by oxidation of 2-methyl-5-ethynylpyridine with perhydrol in acetic anhydride. The synthesis of N-oxides of pyridylacetylenic amines by the Mannich reaction carried out. The effect of the solvents: methanol, ethanol and n-dioxane, the catalyst, and the reaction time on the yield of the final product studied. The structure and composition of the synthesized PAA N-oxides were established using IR and PMR spectroscopy.

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