{"id":"W2058749895","doi":"10.1021/jo202681r","title":"Unexpected 5,6,7,8,9,10-Hexahydro-6,6-pentamethylenephenanthridines and 2,3,4,5-Tetrahydro-4,4-tetramethylene-1<i>H</i>-cyclopenta[<i>c</i>]quinolines from Skraup–Doebner–Von Miller Quinoline Synthesis and Their Implications for the Mechanism of That Reaction","year":2012,"lang":"en","type":"article","venue":"The Journal of Organic Chemistry","topic":"Chemical synthesis and alkaloids","field":"Chemistry","cited_by":35,"is_retracted":false,"has_abstract":true,"ca_institutions":"McGill University","funders":"","keywords":"Quinoline; Aniline; Chemistry; Annulation; Derivative (finance); Ring (chemistry); Ketone; Stereochemistry; Amine gas treating; Schiff base; Organic chemistry","routes":{"ca_aff":true,"ca_fund":false,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":false},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0001296067,0.0004268525,0.000137484,0.0002125233,0.0001822818,0.0001742625,0.0004448162,0.0003214638,0.002200801],"category_scores_gemma":[0.0001823857,0.0001650152,0.0002106803,0.0001325654,0.0002737329,0.0004629519,0.0003263524,0.0005453629,0.0007254675],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0001847809,"about_ca_system_score_gemma":0.0003087169,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0002966314,"about_ca_topic_score_gemma":0.001014266,"domain_scores_codex":[0.9999092,0.00001650992,0.000007236308,0.00002386387,0.00001918136,0.00002396378],"domain_scores_gemma":[0.9999274,0.000008784749,0.00002233093,0.00001186693,0.00001224906,0.00001738954],"domain_codex":null,"domain_gemma":null,"domain_candidate":null,"domain_consensus":null,"study_design_codex":"bench_or_experimental","study_design_gemma":"bench_or_experimental","study_design_scores_codex":[0.000157027,0.0001023814,0.000362508,0.0007370646,0.00003432652,0.001108182,0.0003306785,0.0009799802,0.9671746,0.005120465,0.001052526,0.02284023],"study_design_scores_gemma":[0.00003793116,0.0009456979,0.001751352,0.00003871376,0.00003422709,0.00121389,0.00008105798,0.001298986,0.9681243,0.0008352232,0.02560304,0.00003548727],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9119594,0.01071512,0.03946444,0.0006312822,0.0003130189,0.0002628677,0.001122011,0.0004511398,0.03508082],"genre_scores_gemma":[0.9712918,0.004535437,0.01515417,0.0001498685,0.00003391895,0.0001082409,0.0006601688,0.00004241826,0.008024004],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.002200801,"threshold_uncertainty_score":0.007362425,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.02142380265558254,"score_gpt":0.2382450057786548,"score_spread":0.2168212031230723,"validation_status":"score_only:v0-immature-baseline","note":"Baseline scores from an immature model (maturity gate not passed). Scores rank; they never assert a category."}}