Rearrangements in the Diterpenoid Series. Part II. The Diazotization of Methyl 15-β-amino-13-isopropyl-17-noratis-13-en-18-oate

1973 ◽  
Vol 51 (14) ◽  
pp. 2323-2337 ◽  
Author(s):  
William A. Ayer ◽  
Pandurang D. Deshpande
Keyword(s):  
Acetic Acid ◽  
Sodium Nitrite ◽  
Nitrous Acid ◽  
Primary Amines ◽  
Simple Method ◽  
Dinitrogen Tetroxide

Treatment of methyl 15-β-amino-13-isopropyl-17-noratis-13-en-18-oate (1b) with sodium nitrite – acetic acid gives rise to a variety of products, including nitrated compounds and norketones. The structures of seven of the products have been established. The reaction of methyl 16-isopropylidene-7,17-secoacon-8(15)-en-18-oate (2) with nitrous acid and with dinitrogen tetroxide is described. A simple method for transforming isocyanates to primary amines is presented.

Synthesis, Characterization, Antimicrobial Screening of 5-Bromobenzofuranyl Aryl Ureas and Carbamates

2019 ◽  
Vol 4 (4) ◽  
pp. 232-235
Author(s):  
H.M. Naveena Kumari ◽  
Manjunath Harihara Mathada ◽  
Mahesh Kumar ◽  
K.T. Suda ◽  
K.M. Basavaraja
Keyword(s):  
Acetic Acid ◽  
Hydrazine Hydrate ◽  
Sodium Nitrite ◽  
Potassium Carbonate ◽  
Anhydrous Potassium Carbonate ◽  
Antimicrobial Activities ◽  
Anhydrous Toluene ◽  
Ethyl Carbamate ◽  
Primary Amines ◽  
Antimicrobial Screening

Present work reports the biologically important benzofuran aryl ureas and carbamates. The benzofuran ring was formed by reacting bromo salicylaldehyde with diethyl bromomalonate in presence of dry acetone and anhydrous potassium carbonate to obtain 5-bromo-2-ethyl carboxylate (1). The obtained ester (1) was converted into corresponding hydrazide (2) by treating with hydrazine hydrate in ethanol. Compound 2 was then converted into 5-bromobenzofuran-2-carbonyl azide (3) by treating it with sodium nitrite in dioxane and acetic acid. The compound 3 is converted into 5-bromobenzofuranyl aryl ureas (4a-e) after treating primary amines and anhydrous toluene. 5-Bromobenzofuranyl aryl carbamate (5) and ethyl carbamate (6) were also synthesized by treating compound 3 with substituted phenol in toluene and ethanol respectively. All the compounds were characterized by NMR, IR and screened for antimicrobial activities.

REARRANGEMENT STUDIES WITH C14: XII. THE REACTION OF NITROUS ACID WITH 2-α- OR 2-β-NAPHTHYLETHYLAMINE-1-C14

1962 ◽  
Vol 40 (6) ◽  
pp. 1130-1133
Author(s):  
A. G. Forman ◽  
C. C. Lee
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Sodium Nitrite ◽  
Nitrous Acid ◽  
Glacial Acetic Acid ◽  
Aqueous Hydrochloric Acid

On treatment with sodium nitrite, 2-α-naphthylethylamine-1-C14 in aqueous hydrochloric acid or glacial acetic acid gives rise to the corresponding alcohol, which shows rearrangement of C14 from the C-1 to the C-2 positions to the extent of 32–35%; the 2-β-naphthyl isomer exhibits 26–28% rearrangement. The significance of these results is discussed.

REARRANGEMENT IN THE REACTION BETWEEN 2-PHENYLETHYLAMINE-1-C14 AND NITROUS ACID

1953 ◽  
Vol 31 (8) ◽  
pp. 761-767 ◽  
Author(s):  
C. C. Lee ◽  
J. W. T. Spinks
Keyword(s):  
Acetic Acid ◽  
Sodium Nitrite ◽  
Nitrous Acid ◽  
Glacial Acetic Acid ◽  
Reaction Intermediates ◽  
Carbonium Ions

On treatment with sodium nitrite, 2-phenylethylamine-1-C14 in aqueous hydrochloric, perchloric, acetic, or glacial acetic acid gives rise to products in which the C14 atoms have been rearranged from the C-1 to the C-2 position to an extent of 20.5 to 22.5%. The results are discussed on the basis of carbonium ions as possible reaction intermediates.

scholarly journals SYNTHESIS OF ESTERS OF HALOGENOACETIC ACIDS

2020 ◽  
Vol 2020 (3) ◽  
pp. 38-43
Keyword(s):  
Acetic Acid ◽  
Acid Catalyst ◽  
Primary Amines ◽  
Primary Alcohols ◽  
Sulfuric Acid Catalyst ◽  
Nucleophilic Exchange ◽  
Pmr Spectra ◽  
High Yields ◽  
Esterification Reactions ◽  
Acetic Acids

Amidoalkylating reagents containing a phthalimide group are used in the synthesis of hard-to-reach primary amines and complex heterocyclic compounds. These types of amidoalkylating compounds are suitable reagents for nucleophilic substituted reactions in acidic media due to their resistance to acids. Result of reactions of amidoalkylating reagents-N-hydroxyethylphthalimide and N-hydroxymethylphthalimide with aliphatic carbonic acids can also produce new bactericidal and fungicidal esters. In this study, halogen acids reacted with N-hydroxymethylphthalimide monochloric acetic acid, monobromic acetic acid, monoiodic acetic acid, trifluoric acetic acid and trichloroacetic acid, as well as, N-b-hydroxyethylphthaleidyl monohydric acid. As a result of the reactions, new phthalimidomethyl and phthalimidoethyl esters of haloacetic acids were synthesized. The physical properties of crystalline esters have been determined. The structure of these compounds were confirmed by the analysis of their IR and PMR spectra. The esterification reactions of halogenated acetic acids were carried out in a benzene solvent and a sulfuric acid catalyst with primary alcohols, N-hydroxymethylphthalimide and N-β- beta hydroxyethylphthalimide,. It was found that in a benzene solvent, which increases the rate of bimolecular nucleophilic exchange in primary alcohols, phthalimidoethyl esters of halogen acid are formed in high yields, and phthalimidomethyl esters are formed in low yields. It was shown that the reaction of esterification of halogen acids with N-hydroxymethylphthalimide proceeds with monomolecular nucleophilic exchange.

scholarly journals Convenient Synthesis of Functionalized Cyclopropa[c]coumarin-1a-carboxylates

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 57 ◽  
Author(s):  
Olga Ivanova ◽  
Vladimir Andronov ◽  
Irina Levina ◽  
Alexey Chagarovskiy ◽  
Leonid Voskressensky ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Aromatic Ring ◽  
Hydroxy Group ◽  
Fine Chemicals ◽  
Simple Method ◽  
Convenient Synthesis ◽  
Donor Acceptor

A simple method has been developed for the synthesis of cyclopropa[c]coumarins, which belong to the donor-acceptor cyclopropane family and, therefore, are promising substrates for the preparation of chromene-based fine chemicals. The method, based on the acetic acid-induced intramolecular transesterification of 2-arylcyclopropane-1,1-dicarboxylates, was found to be efficient for substrates containing hydroxy group directly attached to the aromatic ring.

scholarly journals Improved Method for the Determination of Anatoxin-a and Two of Its Metabolites in Blue-Green Algae Using Liquid Chromatography with Fluorescence Detection

2005 ◽  
Vol 88 (6) ◽  
pp. 1741-1747 ◽  
Author(s):  
Dorothea F K Rawn ◽  
Benjamin P-Y Lau ◽  
Barbara Niedzwiadek ◽  
James F Lawrence
Keyword(s):  
Liquid Chromatography ◽  
Green Algae ◽  
Fluorescence Detection ◽  
Background Noise ◽  
Degradation Products ◽  
Food Supplements ◽  
Primary Amines ◽  
Algal Toxins ◽  
Simple Method ◽  
Blue Green Algae

Abstract Anatoxin-a, a neurotoxin produced by blue-green algae (BGA) species, can cause death to exposed organisms. In North America, BGA are harvested and sold as food supplements, some of which contain elevated levels of other algal toxins, such as microcystins. Concern that elevated levels of anatoxin-a also may be present in BGA food supplements has led to the development of a simple method to determine the presence of anatoxin-a in BGA. Some researchers have successfully analyzed this compound using liquid chromatography with fluorescence detection by forming a fluorescent derivative with 4-fluoro-7-nitrobenzofurazan (NBD-F) in water and phytoplankton extracts. With this method, the background noise is high in BGA extracts due to the presence of co-extractives. Addition of o-phthaldialdehyde (OPA) and mercaptoethanol to the extract before addition of the NBD-F resulted in the successful removal of primary amines from the background noise when the NBD-F derivatives were detected with fluorescence. Improved chromatograms were obtained when extracts were cleaned up in this manner, leading to a lower detection limit (approximately 50 μg/kg) for anatoxin-a. The detection limits obtained for the 2 degradation products dihydroanatoxin-a and epoxyanatoxin-a in BGA extracts were similarly low (55 and 65 μg/kg, respectively).

scholarly journals Visual inspection of cervix with acetic acid as a feasible screening test for cervical neoplasia among women attending at OPD in Rajshahi Medical College Hospital

KYAMC Journal ◽  
2018 ◽  
Vol 9 (2) ◽  
pp. 56-60
Author(s):  
Nahid Yusuf ◽  
Md Ahmed Ali ◽  
Nazmun Nahar ◽  
Shipra Chaudhury ◽  
Md Zillur Rahman
Keyword(s):  
Acetic Acid ◽  
Predictive Value ◽  
Urban Areas ◽  
Visual Inspection ◽  
Pap Smear ◽  
Low Cost ◽  
Low Grade ◽  
College Hospital ◽  
Health Care Centre ◽  
Simple Method

Background: Visual inspection of cervix after application of 3-5% acetic acid (VIA) is a potential alternative to Pap smear cytology for screening of cervical cancer in resource poor settings.Objectives: This study was to evaluate the performance of visual inspection based screening approach in the detection of precancerous and early cancerous lesions of the cervix.Materials & Methods: VIA was carried out in 540 eligible women attending Gynae OPD. Detection of well-defined, opaque, acetowhite lesion close to squamocolumnar junction or in transitional zone of the cervix constituted positive VIA. All screened women evaluated by colposcopy and biopsy were taken from colposcopically suspected areas. The final diagnosis was based on histology.Results: Out of 540 patients, 328 were VIA negative and 212 were VIA positive. Colposcopy showed normal results in 340 cases, low grade CIN in 138 cases, high grade CIN in 44 cases and cancer in 18 cases. There were biopsy proven chronic cervicitis and metaplastic changes in 423 cases, CIN I in 66 cases, CIN II in 25 cases, CIN III / carcinoma-in-situ in 5 cases. The sensitivity of VIA was 74.36%, specificity 70.45%, positive predictive value 41.04%, & negative predictive value 90.85%.Conclusion: VIA can differentiate a normal cervix from a precancerous cervix with reasonable accuracy. As it is low cost and simple method, it can be set in any hospital or any health care centre of rural or urban areas of poor resource settings.KYAMC Journal Vol. 9, No.-2, July 2018, Page 56-60

scholarly journals Determination of Diethanolamine in Shampoo Products Containing Fatty Acid Diethanolamides by Liquid Chromatography with a Thermal Energy Analyzer

2005 ◽  
Vol 88 (2) ◽  
pp. 592-594 ◽  
Author(s):  
Hardy J Chou
Keyword(s):  
Acetic Acid ◽  
Liquid Chromatography ◽  
Fatty Acid ◽  
Thermal Energy ◽  
Sodium Nitrite ◽  
Room Temperature ◽  
Energy Analyzer

Abstract A liquid chromatography (LC) method using a thermal energy analyzer (TEA) is described for the determination of diethanolamine (DEA) in shampoo products containing fatty acid diethanolamides. DEA was converted to N-nitrosodiethanolamine (NDELA) by dissolving a portion of the product in 6M acetic acid and mixing with sodium nitrite for 1 h at room temperature. The reaction mixture was dried, dissolved in acetone, and analyzed for NDELA by LC-TEA. The recovery of DEA from 2 shampoo products at fortification levels of 25, 250, and 1000 ppm ranged from 70 to 105%. Twenty shampoo products were analyzed by this method, and 19 were found to contain DEA at levels ranging from 140 to 15 200 ppm.

Sign in / Sign up

Export Citation Format

Share Document