Dibenzo[b,e][1,4]diazepines

Ar, Hanze; Re, Strube; Me, Greig

doi:10.1021/jm00342a031

Cited by 23 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, the bridging benzene ring fixes the orientation of both amide groups in the same direction, as in the β conformation of 1. Compound 14 was prepared by modification of a literature route 22 as outlined in Scheme 3. (Table 1, Entry 6).…”

Section: Resultsmentioning

confidence: 99%

Studies on the preparation and crystal polymorphism of 2-acetamidobenzamide and related compounds

Kelleher¹,

McAuliffe²,

Moynihan³

et al. 2007

Arkivoc

View full text Add to dashboard Cite

2-Acetamidobenzamide 1 exists in two crystal polymorphic forms: α and β. The α form features an approximately planar molecular conformation and an intramolecular N−H...O hydrogen bond. In the β form, the amido groups are out of the plane of the benzene ring and no intramolecular hydrogen bonds are present. In our study, the α form was found to be the more readily obtainable initially, usually as well-formed needles. 2-Acetamido-4-chlorobenzamide 8 and 2-acetamido-5-chlorobenzamide 9 were prepared and assessed as additives in recrystallizations of 2-acetamidobenzamide. In the presence of compound 8, attempted recrystallization of 2-acetamidobenzamide gave crystals of the anhydrous form of 2-methylquinazol-4-one 4. Addition of compound 9 had no effect on the crystal form obtained. 10,11-Dihydro-5-acetyldibenzo [b,e][1,4]diazepin-11-one 14 was prepared as a conformational mimic of the molecular conformation of the β form of 2-acetamidobenzamide. Compound 14 had no effect on the recrystallization of 2-acetamidobenzamide from acetone when added in 10% w/w or from water when added in 1% w/w. When 14 was added in 10% w/w quantities to crystallizations of 2-acetamidobenzamide from water, fine crystallites were obtained which gave infra-red spectra consistent with the α form, but gave PXRD patterns suggesting the presence of another form or compound. Disruption of the intramolecular hydrogen bonds in the α form of 2-acetamidobenzamide 1 by direct trimethylsilylation gave mixtures of 1 and 2-methylquinazol-4-one 4. Indirect trimethylsilylation by reaction of 2-methyl-4H-benzo [d] [1,3]oxazin-4-one 3 with tris(trimethylsilyl)amine gave crystals of the anhydrous form of 2-methylquinazol-4-one 4. 2-Phthalimidobenzoic acid 18 and 2-phthalimidobenzamide 19 were prepared as structural analogues of compound 1 which are incapable of possessing an intramolecular hydrogen bond. Addition of compound 18 to recrystallizations of 2-acetamidobenzamide 1 had no effect on the outcome. However addition of compound 19 resulted in needle-like crystals of the α form of considerably reduced dimensions.

show abstract

Section: Resultsmentioning

confidence: 99%

Studies on the preparation and crystal polymorphism of 2-acetamidobenzamide and related compounds

Kelleher¹,

McAuliffe²,

Moynihan³

et al. 2007

Arkivoc

View full text Add to dashboard Cite

show abstract

“…Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. (Hanze et al, 1963). They display wide variety of biological properties, including antidepressant (Beccalli et al, 2005), antimicrobial (Farnet et al, 2005), analgesic and anti-inflammatory (Joergensen et al, 1996), antitumor (McAlpine et al, 2008 activities, while the dibenzodiazepin-1-ones are hepatitis C virus (HCV) NS5B polymerase inhibitors (McGowan et al, 2009).…”

Section: Methodsmentioning

confidence: 99%

“…For details of the synthesis, see: Hanze et al (1963); Rashed et al (1993); Kolos et al (2004); Corté s et al (2007); Ajani et al (2010). For the biological activity of dibenzo [b,e] [1,4]diazepinones, see: Beccalli et al (2005); Farnet et al (2005); Joergensen et al (1996); McAlpine et al (2008); McGowan et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

11-(4-Methoxyphenyl)-3,3-dimethyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate

et al. 2012

View full text Add to dashboard Cite

In the title compound, C22H24N2O2·H2O, the co-crystallized water molecule interacts with the N and O atoms of the molecule through Ow—H⋯N, Ow—H⋯O(methyl) and N—H⋯Ow hydrogen-bonding interactions. These hydrogen bonds, along with the intermolecular N—H⋯O=C hydrogen-bonding interactions, connect the molecules into a three-dimensional network. The dihedral angle between the two aromatic rings is 65.46 (10)°.

show abstract

“…However, less attention has been paid to the convergent synthesis of skeleton 2 . The available procedure relies on the reduction of 1a to give 2 in <50 % yield (Scheme ) 2,4a…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Insights into the Palladium‐Catalyzed Domino Synthesis of 10,11‐Dihydro‐5H‐dibenzo[b,e][1,4]diazepines

Laha¹,

Tummalapalli²,

Gupta³

2014

Eur J Org Chem

View full text Add to dashboard Cite

A palladium‐catalyzed domino approach to the synthesis of 10,11‐dihydro‐5H‐dibenzo[b,e][1,4]diazepines starting from o‐phenylenediamines and 2‐bromobenzyl bromides or tosylates has been developed. Mechanistic studies support the following domino sequence. Intermolecular mono‐N‐benzylation of the o‐phenylenediamine through oxidative palladium insertion, primarily at the benzylic position of the 2‐bromobenzyl bromide, is followed by intramolecular N′‐arylation. The intramolecular N′‐arylation is demonstrated to be facilitated by coordination of a remote auxiliary nitrogen atom to the palladium atom.

show abstract

Dibenzo[b,e][1,4]diazepines

Cited by 23 publications

References 0 publications

Studies on the preparation and crystal polymorphism of 2-acetamidobenzamide and related compounds

Studies on the preparation and crystal polymorphism of 2-acetamidobenzamide and related compounds

11-(4-Methoxyphenyl)-3,3-dimethyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate

Mechanistic Insights into the Palladium‐Catalyzed Domino Synthesis of 10,11‐Dihydro‐5H‐dibenzo[b,e][1,4]diazepines

Contact Info

Product

Resources

About