A Facile Synthesis, Spectroscopic Identification, and Antimicrobial Activities of Some New Heterocyclic Derivatives from D-erythro-2,3-hexodiuloso-1,4-lactone-2-(o-chlorophenyl hydrazone)-3-oxime
Notice bibliographique
Résumé
A new series of different heterocyclic derivatives was prepared via a facile unimolecular condensation of D-iso ascorbic acid with o-chlorophenyl hydrazine to give D-erythro-2,3-hexodiulosono-1,4-lactone 2-( o-chlorophenyl hydrazine (2). Reactions of (2) with hydroxylamine gave the 2-( o-chlorophenyl hydrazone)-3-oxime (3). On boiling with boiling acetyl chloride, (3) gave 2-o-chlorophenyl-4-(2,3-di-O-acetyl-D-erythro-glyceryl-1-yl)-1,2,3-triazole-5-carboxylic acid-5,1́-lactone (4). In the treatment of (3) with benzoyl chloride in pyridine the same dehydrative cyclization occurred giving, 2-o-chlorophenyl-4-(2,3-di-o-benzoyloxy-D-erythro-glycerol-1-yl)-1,2,3-triazole-5-carboxylic acid-5,1΄-lactone (5). On the treatment of compound (4) with liquid ammonia in methanol, deacetylation occurred concurrently with the opening of the lactone ring, to afford the 2-o-chlorophenyl-4-(D-erythro-glycerol-1-yl)-1,2,3-triazole-5-carboxamide (6). Similarly, treatment of compound (4) with hydrazine hydrate in methanol, afforded 2-o-chlorophenyl-4-(D-erythro-glycerol-1-yl)-1,2,3-triazole-5-carboxylic acid hydrazide (7). The controlled reaction of (3) with sodium hydroxide, followed by neutralization, gave 3-(D-erythro-glycerol-1-yl)-4,5-isoxazoline-5-(4H)-one-4-o-chlorophenyl hydrazone (8). Reaction of (3) with HBr-AcOH gave 5-O-acetyl-6-bromo-6-deoxy-D-erythro-2,3-hexodiulosono-1,4-lactone-2-(o-chlorophenyl hydrazone)-3-oxime (9); these were converted into 4-(2-O-acetyl-3-bromo-3-deoxy-l-threo-glycerol-l-yl)-2-aryl-1,2,3-triazole-5-carboxylic acid 5,41-lactones on treatment with acetic anhydride-pyridine. Compound (3) treatment with bromine-water caused its cyclization and bromination of the phenyl group to give carboxylic acid 5,1΄-lactone (10). Acetylation of (10) gave the diacetate (11), which upon treatment with hydrazine hydrate in methanol, afforded compound (12), mild acetylation of compound (12) gave the triacetate (13) boiling of (13) with acetic anhydride afforded hexa acetyl derivative (14). on the treatment of compound (11) with liquid ammonia in methanol deacetylation occurred to afford 1,2,3-triazole-5-carboxamide derivative (15). On the other hand, treatment of compound (3) with bromine-water for a short time yielded 3-oxime (16). Subsequent acetylation with boiling acetic anhydride afforded compound (11). In addition, acetylation of compound 3 afforded a diacetyl derivative assigned as 5,6-di-O-acetyl-D-erythro-2,3-hexodilusono-1,4-lactone-(2-o-chlorophenyl hydrazone)-3-acetoxime (17), which on boiling with acetic anhydride cyclization occurred giving compound (4). On the treatment of Dehydro-L-ascorbic acid-2-phenyl hydrazone (L-threo-2,3-hexodiulosono- 1,4-lactone 2-phenylhydrazone (19) with acetic anhydride/pyridine, afforded 5,6-di-O-acetyl-3-acetoxime (20) that upon treatment with boiling acetic anhydride, afforded the triazole derivative (21). Furthermore, treatment of the monophenyl hydrazone (18) with S-benzyl hydrazine carbodithiolate in the presence of acetic acid, afforded the bis-hydrazone, L-threo-2,3-hexodilusono-1,4-lactone-3-(S-benzylhydrazinocarbodithiolate)-2-phenylhydrazone (22). Acetylation of compound (22) with acetic anhydride and pyridine did not give the di-O-acetyl derivative expected but instead, elimination of a molecule of acetic acid and partial hydrolysis of a hydrazone residue took place to give compound (23). The structures of all the synthesized compounds were confirmed using elemental analysis and different spectral tools. Eight samples from the synthesized compounds, 2,3, 4,10.16,11,12,17 were tested for their antimicrobial activity and they showed no activities.
Récupéré en direct depuis OpenAlex et désinversé. Les résumés ne sont pas conservés dans cette base de données : les index inversés représentent 8,6 Go des 9,3 Go de texte de la base, et le serveur dispose de 13 Go libres.
Comment cette classification a été obtenuedéplier
Prédiction machine sur la base complète
Imitation des enseignantsNi prévalence calibrée, ni vérité terrain. Validation humaine à venir. Le volet Gemma est une étiquette directe du modèle pour chaque travail de la base, lue sur la notice réduite au titre. Le volet Codex est un classifieur appris des 10 348 étiquettes directes de Codex et calibré sur les taux pondérés de l'échantillon; les champs sans appui suffisant ne portent aucun appel Codex. Le mode candidate est l'union des deux volets; le consensus est leur intersection. Ces sorties portent le statut machine_predicted_unvalidated et ne sont pas des étiquettes humaines.
Scores du classifieur distillé par catégorie (deux têtes)
| Catégorie | Codex | Gemma |
|---|---|---|
| Métarecherche | 0,000 | 0,000 |
| Méta-épidémiologie (sens strict) | 0,000 | 0,000 |
| Méta-épidémiologie (sens large) | 0,000 | 0,000 |
| Bibliométrie | 0,000 | 0,000 |
| Études des sciences et des technologies | 0,000 | 0,000 |
| Communication savante | 0,000 | 0,000 |
| Science ouverte | 0,000 | 0,000 |
| Intégrité de la recherche | 0,000 | 0,000 |
| Charge utile insuffisante (le modèle a refusé de juger) | 0,001 | 0,000 |
Scores machine (provisoires)
Les deux têtes enseignantes du modèle étudiant, lues sur ce travail. Un score ordonne la base pour la relecture; il n'affirme jamais une catégorie, et le statut de validation accompagne chaque rangée tel quel.
Scores de référence d'un modèle non mature (critères de maturité non atteints, 7 itérations). Un score ordonne; il n'affirme jamais une catégorie.
score_only:v0-immature-baseline · tel quel depuis la passe de notation : score_only signifie que le nombre peut ordonner les travaux, et qu'aucune étiquette de catégorie n'en découleClassification
machine, non validéePrédiction automatique; un appel candidat d’une seule source (Gemma direct ou Codex distillé), pas un consensus.
Le détail, modèle par modèle et score par score, se trouve en fin de page sous « Comment cette classification a été obtenue ».