4,5-Dihydro-3H-benzo[c]azepines from 1,7-electrocyclization reactions of 2-aza-4,5-benzoheptatrienyllithium compounds

European Journal of Organic Chemistry

Volumn , Issue 16, 2004, Pages 3465-3476

  Gerdes, Klaus ^a   Sagar, Pramod ^a   Fröhlich, Roland ^a   Wibbeling, Birgit ^a   Würthwein, Ernst Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

1,7 Anionic electrocyclization reaction; 2 Azaheptatrienyl anions; Dihydrobenzo c azepines; Lithium compounds; Quantum chemical calculations

Indexed keywords

2 AZA 4,5 BENZOHEPTATRIENYLLITHIUM; 4 METHYL 3 PHENYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 4,5 DIHYDRO 3 H BENZ[C]AZEPINE; 4,5 DIMETHYL 3 PHENYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 5 ALLYL 3 PHENYL 4 PROPYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 5 ALLYL 4 METHYL 3 PHENYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 5 BENZYL 3 PHENYL 4 PROPYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 5 BENZYL 4 METHYL 3 PHENYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 5 ETHYL 3 PHENYL 4 PROPYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 5 ETHYL 4 METHYL 3 PHENYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 5 ETHYL 4 METHYL 3 VINYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; 5 METHYL 4 PROPYL 3 VINYL 4,5 DIHYDRO 3H BENZ[C]AZEPINE; ALLYL(2 PENT 1 ENYLBENZYLIDENE)AMINE; ALLYL(2 PROPENYLBENZYLIDENE)AMINE; AMIDE; AMINE; ANION; AZEPINE DERIVATIVE; BENZALDEHYDE; BENZYL(2 PENT 1 ENYLBENZYLIDENE)AMINE; BENZYL(2 PROPENYLBENZYLIDENE)AMINE; BENZYL(2 STYRYLBENZYLIDE)AMINE; BENZYLAMINE; DIMER; IMINE; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CYCLIZATION; ENERGY; OLEFINATION; POLYMERIZATION; QUANTUM CHEMISTRY; REACTION ANALYSIS; SOLID STATE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 4544275676     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400206     Document Type: Article

References (35)

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16. Data sets were collected with Enraf Nonius CAD4 and Nonius KappaCCD diffractometers, which, in the case of Mo radiation, were equipped with a rotating anode generator Nonius FR591. Programs used: data collection: EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction: MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data: SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution: SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473), structure refinement: SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics: SCHAKAL (E. Keller, University Freiburg, 1997). CCDC-230966 [(3R*,4S*)-6f], -230967 (8), -230968 [(3R*,4S*,5S*)-6d], -230970 [(3R*,4R*,5R*)-6b], -230971 [(3R*,4R*,5R*)- 6c], and -230972 [(E)-4gg] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/ conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk].
17. Data sets were collected with Enraf Nonius CAD4 and Nonius KappaCCD diffractometers, which, in the case of Mo radiation, were equipped with a rotating anode generator Nonius FR591. Programs used: data collection: EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction: MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data: SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution: SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473), structure refinement: SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics: SCHAKAL (E. Keller, University Freiburg, 1997). CCDC-230966 [(3R*,4S*)-6f], -230967 (8), -230968 [(3R*,4S*,5S*)-6d], -230970 [(3R*,4R*,5R*)-6b], -230971 [(3R*,4R*,5R*)- 6c], and -230972 [(E)-4gg] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/ conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk].
18. Data sets were collected with Enraf Nonius CAD4 and Nonius KappaCCD diffractometers, which, in the case of Mo radiation, were equipped with a rotating anode generator Nonius FR591. Programs used: data collection: EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction: MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data: SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution: SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473), structure refinement: SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics: SCHAKAL (E. Keller, University Freiburg, 1997). CCDC-230966 [(3R*,4S*)-6f], -230967 (8), -230968 [(3R*,4S*,5S*)-6d], -230970 [(3R*,4R*,5R*)-6b], -230971 [(3R*,4R*,5R*)- 6c], and -230972 [(E)-4gg] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/ conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk].
19. Data sets were collected with Enraf Nonius CAD4 and Nonius KappaCCD diffractometers, which, in the case of Mo radiation, were equipped with a rotating anode generator Nonius FR591. Programs used: data collection: EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction: MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data: SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution: SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473), structure refinement: SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics: SCHAKAL (E. Keller, University Freiburg, 1997). CCDC-230966 [(3R*,4S*)-6f], -230967 (8), -230968 [(3R*,4S*,5S*)-6d], -230970 [(3R*,4R*,5R*)-6b], -230971 [(3R*,4R*,5R*)- 6c], and -230972 [(E)-4gg] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/ conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk].
20. Data sets were collected with Enraf Nonius CAD4 and Nonius KappaCCD diffractometers, which, in the case of Mo radiation, were equipped with a rotating anode generator Nonius FR591. Programs used: data collection: EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction: MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data: SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution: SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473), structure refinement: SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics: SCHAKAL (E. Keller, University Freiburg, 1997). CCDC-230966 [(3R*,4S*)-6f], -230967 (8), -230968 [(3R*,4S*,5S*)-6d], -230970 [(3R*,4R*,5R*)-6b], -230971 [(3R*,4R*,5R*)- 6c], and -230972 [(E)-4gg] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/ conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk].
21. Data sets were collected with Enraf Nonius CAD4 and Nonius KappaCCD diffractometers, which, in the case of Mo radiation, were equipped with a rotating anode generator Nonius FR591. Programs used: data collection: EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction: MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data: SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426), structure solution: SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473), structure refinement: SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics: SCHAKAL (E. Keller, University Freiburg, 1997). CCDC-230966 [(3R*,4S*)-6f], -230967 (8), -230968 [(3R*,4S*,5S*)-6d], -230970 [(3R*,4R*,5R*)-6b], -230971 [(3R*,4R*,5R*)- 6c], and -230972 [(E)-4gg] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/ conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) + 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk].
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