The first benzodiazepine o-quinodimethane: Generation and Diels-Alder reactions

Tetrahedron Letters

Volumn 44, Issue 10, 2003, Pages 2007-2009

  Pozarentzi, Minothora ^a   Stephanidou Stephanatou, Julia ^a   Tsoleridis, Constantinos A ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Benzodiazepines; Diels Alder reactions; o quinodimethanes

Indexed keywords

7,8 BIS(DIBROMOMETHYL) 3 BROMO 2,4 DIPHENYL 3H BENZODIAZEPINE; BENZODIAZEPINE DERIVATIVE; BENZODIAZEPINE O QUINODIMETHANE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; PRECURSOR;

BETULACEAE;

EID: 0037416835     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00233-8     Document Type: Article

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24. +; (b) due to the hindered inversion of the diazepine ring, the methylene protons of the achiral compound 8 are differentiated and give very broad singlets at δ=1.68 and 3.83. The signal at 1.68 can be assigned to the proton in the endo site of the diazepine ring, where it is shielded by both C=N anisotropy cones (+). On the other hand, the exo proton being closer to the deshielding cones of the two phenyls and of the two C=N bonds resonates at much lower field. The same discrimination of the methylene protons is observed in all other derivatives 3-7.