Nitrobenzoyl derivatives

Ring enlargement of A-acyl compounds, generally observed with oxaziridines, is observed only occasionally with diaziridines. Under more forced conditions of acylation with acetic anhydride, oxadiazolines like (139) were obtained (76MIP50800). A 4-nitrobenzoyl derivative rearranged at room temperature (76JOC3229). 

These formulae explain the scission products of the two alkaloids and the conversion of evodiamine into rutaecarpine, and were accepted by Asahina. A partial synthesis of rutaecarpine was effected by Asahina, Irie and Ohta, who prepared the o-nitrobenzoyl derivative of 3-)3-amino-ethylindole-2-carboxylic acid, and reduced this to the corresponding amine (partial formula I), which on warming with phosphorus oxychloride in carbon tetrachloride solution furnished rutaecarpine. This synthesis was completed in 1928 by the same authors by the preparation of 3-)S-amino-ethylindole-2-carboxylic acid by the action of alcoholic potassium hydroxide on 2-keto-2 3 4 5-tetrahydro-3-carboline. An equally simple synthesis was effected almost simultaneously by Asahina, Manske and Robinson, who condensed methyl anthranilate with 2-keto-2 3 4 5-tetrahydro-3-carboline (for notation, see p. 492) by the use of phosphorus trichloride (see partial formulae II). Ohta has also synthesised rutaecarpine by heating a mixture of 2-keto-2 3 4 5-tetrahydrocarboline with isatoic anhydride at 195° for 20 minutes. 

Cevadine contains neither a methoxyl nor a methylimino group it yields crystalline benzoyl and o-nitrobenzoyl derivatives, m.p. 255° and 236° respectively, and a methiodide, which decomposes at 210-2°, and is converted by silver oxide into eevadinemethylhydroxide.i When warmed with alcoholic soda, cevadine undergoes hydrolysis into eevine and angelic and tiglic acids. When hydrogen chloride is passed into cevadine in alcohol, ethyl tiglate and eevine are formed. ... 

Reactivity of substituents attached to ring heteroatoms 5.2.2.7 Alkyl groups and further carbon functional groups. The N-2-nitrobenzoyl derivative of indolo benzazepine 384a can be easily deprotected on the indole nitrogen by treatment with N,N-diethylaminoethylamine in DMF at room temperature (Scheme 79, Section 5.1.2 (1991JHC379)). 

Suzuki, A. Handa, S, Yamakawa, Y. Separation of molecular species of higher glycolipids by high performance liquid chromatography of their 0-acetyl-N-p-nitrobenzoyl derivatives. 

The stereochemistry of the cyclopropyl as well as oxirane moiety in these P-lactams was determined based on the single crystal X-ray analysis of P-lactam 34 and the 4-nitrobenzoyl derivative (37) of 3-hydroxy-P-lactam 32.71 The extremely high diastereoselectivity observed in these cyclopropanation and epoxidation reactions can be explained by taking into account the highly organized transition state structures illustrated in Figure 1. The directing effect of the C-3... 

The use of negative ions produced by the electron capture ionization may constitute another alternative for increasing sensitivity. Stapleton and Bowie [226] applied this method to the study of the structures of the nitrobenzoyl derivatives of various natural amino acids. All the species studied led to clear-cut and interpretable fragmentations, enabling the structure of the amino acid in question to be determined. 

The mass spectra of the o-nitrobenzoyl derivatives may be interpreted according to classical mechanisms (as ortho effects). In the case of m-nitro compounds, however, only the molecular anion is present in addition to the m/z 46 (NO2 ) ion. The solution to this problem involves rescanning in positive mode in order to increase the number of fragments. This operation is not easy and it is more advantageous to measure... 

Ishikawa and Fletcher94 prepared 2-0-benzyl-3,4,6-tri-0-(p-nitro-benzoyl)-, 2,3-di-0-benzyl-4,6-di-0-(p-nitrobenzoyl)-, and 2,3,4-tri-O-benzyl-6-0-(p-nitrobenzoyl)-/8-D-glucopyranosyl bromides from the corresponding l-O-(p-nitrobenzoyl) derivatives by the action of hydrogen bromide in dichloromethane. These compounds are now often... 

The conclusions drawn from acyl migration experiments have been corroborated by a series of additional experimental facts. Nor->fi-tropine furnished a meta-oxazine derivative (V) (m.p. 101°) (8) with p-nitrobenzaldehyde as contrasted with nor-tropine (IV H instead of CH3), which gave only the Af-p-nitrobenzoyl derivative (VI) (8) on similar treatment. 

Reduction of the o-nitrobenzoyl derivative of 185 (R = NH2) with Raney nickel and hydrogen brings about ring transformation to 5,6,7,8-tetrahydro-2-(o-aminophenyl)pyrimidin-4-one.269... 

Anhalamine was first isolated by Kauder (5). According to Heffter (11) the drug contains 0.1 % anhalamine. The base crystallizes in microscopic needles, m.p. 189-191° hydrochloride, from water with 2 H2O, m.p. 258° from alcohol with 1 H2O sulfate, colorless prisms, very soluble in water, less in alcohol well-crystallized platinichloride and aurichloride picrate, m.p. 237-240° monobenzoyl derivative, m.p. 167.5° dibenzoyl derivative, m.p. 128-129° iV-m-nitrobenzoyl derivative, m.p. 174-175° 0,A -dimethyl-anhalamine methiodide, m.p. 211.5-212.5°. 

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