{"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":"codex-gemma-dda1882f352a","candidate_categories":["metaepi_narrow","insufficient_payload"],"consensus_categories":[],"category_scores_codex":[0.0007642257,0.0004508304,0.0007314378,0.00003887218,0.0003111729,0.00005355797,0.0006915698,0.0002736266,0.0009789317],"category_scores_gemma":[0.0008210455,0.0002525233,0.0002794437,0.0002074395,0.0003439571,0.0002434656,0.0002180709,0.0004317641,0.000001164528],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0000989656,"about_ca_system_score_gemma":0.00006882982,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.00006576912,"about_ca_topic_score_gemma":0.00001004749,"domain_scores_codex":[0.9980474,0.0000645469,0.000870159,0.0002916671,0.0002662076,0.0004600465],"domain_scores_gemma":[0.9936923,0.004107041,0.001058269,0.0006836411,0.0002216568,0.0002371151],"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":[0.0002004488,0.0002029109,0.000718536,0.0001397113,0.0004268397,2.497787e-7,0.0005018099,7.247264e-7,0.9903744,0.00001685522,0.0003388599,0.007078678],"study_design_scores_gemma":[0.0006069829,0.0000201731,0.0007113642,0.0002107298,0.0006595961,0.0002127443,0.002242748,0.00004042764,0.9892363,0.0009977334,0.004764285,0.0002969302],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9826826,0.0138545,0.0005828411,0.002103678,0.00013192,0.000174838,0.0002422353,0.00003137933,0.0001959641],"genre_scores_gemma":[0.9884901,0.00988838,0.0003819776,0.00006574986,0.0009243683,0.0000282054,0.00002263521,0.00007645845,0.0001221358],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.006781748,"threshold_uncertainty_score":0.9999927,"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."}}