An aza cyclopropylcarbinyl-homoallyl radical rearrangement-radical cyclization cascade. Synthesis of dibenzoimidazoazepine and oxazepine derivatives

Journal of Organic Chemistry

Volumn 76, Issue 13, 2011, Pages 5384-5391

  Khlebnikov, Alexander F ^a   Novikov, Mikhail S ^a   Petrovskii, Petr P ^a   Stoeckli Evans, Helen ^b  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b UNIVERSITY OF NEUCHÂTEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINES; CYCLOADDUCTS; DFT-B3LYP; DOUBLE BONDS; ENERGY PROFILE; POLYHETEROCYCLIC SYSTEMS; RADICAL INITIATORS;

HEATING; TOLUENE;

CYCLIZATION;

1 ARYL 1,11B DIHYDROAZIRINO[1,2-D]DIBENZ[B,F][1,4]OXAZEPINE; 1 PHENYL 7,11B DIHYDRO 1H AZIRINO[1,2-A]DIBENZO[C,F]AZEPINE; 10A PHENYL 11,15B DIHYDRO 10AH DIBENZO [B,F]INDENO[2',1':4,5]IMIDAZO[1,2-D][1,4]OXAZEPINE; 10A PHENYL 5,10A,11,15B TETRAHYDRODIBENZO [C,F]INDENO[2',1':4,5]IMIDAZO[1,2-A]AZEPINE; 13,13A DI(2 BROMOPHENYL) 13,13A DIHYDRO 1H,2AH AZIRENO[1',2':3,4]IMIDAZO[1,2-D]DIBENZO[B,F][1,4]OZAXEPINE; 13,13A DIPHENYL 13,13A DIHYDRO 1H,2AH AZIRENO[1',2':3,4]IMIDAZO[1,2-D]DIBENZO[B,F][1,4]OXAZEPINE; 13,13A DIPHENYL 2A,7,13,13A TETRAHYDRO 1H AZIRENO[1',2':3,4]IMIDAZO[1,2-A]DIBENZO[C,F][1,4]AZEPINE; 13A (4 METHOXYPHENYL) 13 PHENYL 13,13A DIHYDRO 1H,2AH AZIRENO[1',2':3,4]IMIDAZO[1,2-D]DIBENZO[B,F][1,4]OXAZEPINE; 13A (4 METHYLPHENYL) 13 PHENYL 13,13A DIHYDRO 1H,2AH AZIRENO[1',2':3,4]IMIDAZO[1,2-D]DIBENZO[B,F][1,4]OXAZEPINE; 15 BROMO 10A (2 BROMOPHENYL) 11,15B DIHYDRO 10AH DIBENZO[B,F]INDENO[2',1':4,5]IMIDAZO[1,2-D][1,4]OXAZEPINE; 1A (4 METHOXYPHENYL) 12 PHENYL 1A,1B DIHYDRO 1H AZIRENO[1',2':3,4]IMIDAZO[1,5-D]DIBENZO[B,F][1,4]OXAZEPINE; 1A (4 METHYLPHENYL) 12 PHENYL 1A,1B DIHYDRO 1H AZIRENO[1',2':3,4]IMIDAZO[1,5-D]DIBENZO[B,F][1,4]OXAZEPINE; 1A (4 NITROPHENYL) 12 PHENYL 1A,1B DIHYDRO 1H AZIRENO[1',2':3,4]IMIDAZO[1,5-D]DIBENZO[B,F][1,4]OXAZEPINE; 1A,12 DI(2 BROMOPHENYL) 1A,1B DIHYDRO 1H AZIRENO[1',2':3,4]IMIDAZO[1,5-D]DIBENZO[B,F][1,4]OZAXEPINE; 1A,12 DIPHENYL 1A,1B DIHYDRO 1H AZIRENO [1',2':3,4]IMIDAZO[1,5-D]DIBENZO[B,F][1,4]OXAZEPINE; 2 (HYDROPEROXYMETHYL) 2,3 DIPHENYL 2,3 DIHYDRODIBENZO[B,F]IMIDAZO[1,2-D][1,4]OXAZEPINE; 3A (4 NITROPHENYL) 13 PHENYL 13,13A DIHYDRO 1H,2AH AZIRENO[1',2':3,4]IMIDAZO[1,2-D]DIBENZO[B,F][1,4]OXAZEPINE; AZEPINE DERIVATIVE; FREE RADICAL; OXAZEPINE DERIVATIVE; PEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; CYCLOADDITION; HEATING; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AZA COMPOUNDS; AZEPINES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOPROPANES; FREE RADICALS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79959672304     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200788k     Document Type: Article

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