N-phenyl-1-aza-2-cyano-1,3-butadienes : An intramolecular hetero diels- alder strategy for the construction of 1,4-benzodiazepines

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4283-4286

  Goulaouic Dubois, Catherine ^d   Adams, David R ^c   Sisti, Nicholas J ^d   Fowler, Frank W ^b   Grierson, David S ^a  

^a CNRS   (France)

^b STONY BROOK UNIVERSITY   (United States)

^c HERIOT WATT UNIVERSITY   (United Kingdom)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; N PHENYL 1 AZA 2 CYANO 1,3 BUTADIENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; DRUG TRANSFORMATION; MOLECULAR INTERACTION; REACTION ANALYSIS;

BETULACEAE;

EID: 0032507926     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00756-4     Document Type: Article

References (21)

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16. 3) δ 1.32-1.82 (m, H-4), 2.14-2.37 (m, H-3), 3.25 and 3.98 (t, J = 13.5 Hz, 1H, H-5), 3.36 (t, J = 11 Hz, H-4a), 5.65-5.79 (s, H-2), 6.2-6.5 (s, H-7); δ 23.8 (C-3), 24.8 (C-4), 47.8 (C-5), 57.2 (C-4a), 63.5 (C-7), 114.8, 118.5 (CN, C-1).
17. 14a = 11.60 min .
18. 14. a) Gilman, N.W.; Rosen, P.; Earley, J.V.; Cook, C.; Todaro, L.J. J. Am. Chem. Soc. 1990, 112, 3969;
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21. 3), indicating that the energy barrier to conformational change (atropisomerism) is 15.25 kcal at 35°C.