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
Bibliographic record
Abstract
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.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".