✦ LIBER ✦

N-Phenyl-1-aza-2-cyano-1, 3-butadienes: An intramolecular hetero Diels-Alder strategy for the construction of 1, 4-benzodiazepines

✍ Scribed by Catherine Goulaouic-Dubois; David R. Adams; Nicholas J. Sisti; Frank W. Fowler; David S. Grierson

Book ID: 104259326
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 189 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00756-4

No coin nor oath required. For personal study only.

✦ Synopsis

A new approach to the construction of tricyclic 1,4-benzodiazepines has been developed, based upon the intramolecular Diels-Alder (IMDA)reaction of 2-cyano-l-azadienes. This study revealed the difficulties inherent to the direct transformation of imine-amide 2 to azadiene 3, but demonstrated the efficiency of the intramolecular [4 + 2] cycloaddition of azadiene 13 as a means to access benzodiazepines 14a,b (3 : 2 mixture; 74% combined yield).

📜 SIMILAR VOLUMES

ChemInform Abstract: N-Phenyl-1-aza-2-cy

ChemInform Abstract: N-Phenyl-1-aza-2-cyano-1,3-butadienes: An Intramolecular Hetero Diels—Alder Strategy for the Construction of 1,4-Benzodiazepines.

✍ C. GOULAOUIC-DUBOIS; D. R. ADAMS; N. J. SISTI; F. W. FOWLER; D. S. GRIERSON 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 3 views

Reactivity of N -Phenyl-1-Aza-2-Cyano-1,

Reactivity of N -Phenyl-1-Aza-2-Cyano-1,3-Butadienes in the Diels−Alder Reaction

✍ Sisti, Nicholas J.; Motorina, Irina A.; Tran Huu Dau, Marie-Elise; Riche, Claude 📂 Article 📅 1996 🏛 American Chemical Society 🌐 English ⚖ 435 KB

ChemInform Abstract: Reactivity of N-Phe

ChemInform Abstract: Reactivity of N-Phenyl-1-aza-2-cyano-1,3-butadienes in the Diels-Alder Reaction.

✍ N. J. SISTI; I. A. MOTORINA; M.-E. TRAN HUU DAU; C. RICHE; F. W. FOWLER; D. S. G 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB

ChemInform Abstract: Synthesis of Perhyd

ChemInform Abstract: Synthesis of Perhydroxazin-4-ones. Competitive Mukaiyama versus Hetero Diels—Alder Reaction in the Cycloaddition of 2-Aza-3-trimethylsilyloxy-1,3-butadiene and Aldehydes.

✍ Alessandro Bongini; Mauro Panunzio; Elisa Bandini; Eileen Campana; Giorgio Marte 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 1 views

Asymmetric synthesis of methyl N-(1-phen

Asymmetric synthesis of methyl N-(1-phenylethyl)-3-aza-10-oxatricyclo[5.2.1.01,5]-4-oxo dec-8-en-6-carboxylate by an intramolecular Diels-Alder reaction

✍ J Zylber; A Tubul; P Brun 📂 Article 📅 1995 🏛 Elsevier Science 🌐 English ⚖ 184 KB

The title compound can be obtained with up to five asymmetric centres of known absolute configuration by a diastereoselective intramolecular Diels-Alder reaction between optically active N-substituted fuffurylamines and maleic anhydride, in which the chirality is transferred from one stereocentre to

Hetero Diels–Alder trapping of 3-methyle

Hetero Diels–Alder trapping of 3-methylene-1,2,4-[3H]naphthalenetrione: an efficient protocol for the synthesis of α- and β-lapachone derivatives

✍ Vijay Nair; P.M Treesa 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 110 KB

3-Methylene-1,2,4-[3H]naphthalenetrione, generated by Knoevenagel condensation of 2-hydroxy-1,4-naphthoquinone with formaldehyde, undergoes facile hetero Diels-Alder reaction with various dienophiles affording derivatives of aand b-lapachone.