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Journal of Chemical Research

2007

DOI: 10.3184/030823407x203387

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A New Way to Quinazolines, Perimidines and Dibenzo[d,f][1,3]Diazepines

Barbara Zaleska

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Bartosz Trzewik

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et al.

Abstract: A synthesis of quinazolines, perimidines and dibenzo [d,f][1,3]diazepines is described. The method involves rearrangements following cyclisation of 2-anilino-2-methoxy-3-oxo-N-phenylbutanethioamides with aromatic 1,3and 1,4-diamines.

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“…For the reaction mechanism, see: Trzewik et al (2010). For similar structures, see: Zaleska et al (2007); Hodorowicz et al (2007). For hydrogen bond graph-set analysis, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

N-(5-Nitropyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide

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et al. 2011

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The title compound, C19H13N5O3, can be obtained from the corresponding α-amido-α-aminonitrone in a reaction with biphenyl-2,2′-diamine. The amido–amidine core has distinctive geometrical parameters including: an outstandingly long Csp 2—Csp 2 single bond of 1.5276 (13) Å and an amidine N—C—N angle of 130.55 (9)°. Intramolecular N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds occur. In the crystal, molecules form layers parallel to (001) via weak intermolecular C—H⋯N interactions. The layers are linked via N—H⋯O hydrogen bonds and π–π interactions along [001] [benzene–pyridine centroid–centroid distance = 3.672 (2) Å].

“…For the reaction mechanism, see: Trzewik et al (2010). For similar structures, see: Zaleska et al (2007); Hodorowicz et al (2007). For hydrogen bond graph-set analysis, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

N-(5-Nitropyridin-2-yl)-5H-dibenzo[d,f][1,3]diazepine-6-carboxamide

¹

,

²

,

³

et al. 2011

Self Cite

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The title compound, C19H13N5O3, can be obtained from the corresponding α-amido-α-aminonitrone in a reaction with biphenyl-2,2′-diamine. The amido–amidine core has distinctive geometrical parameters including: an outstandingly long Csp 2—Csp 2 single bond of 1.5276 (13) Å and an amidine N—C—N angle of 130.55 (9)°. Intramolecular N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds occur. In the crystal, molecules form layers parallel to (001) via weak intermolecular C—H⋯N interactions. The layers are linked via N—H⋯O hydrogen bonds and π–π interactions along [001] [benzene–pyridine centroid–centroid distance = 3.672 (2) Å].

A New Way to Quinazolines, Perimidines and Dibenzo[d,f][1,3]diazepines.

¹

,

²

,

³

et al. 2007

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A New Way to Quinazolines, Perimidines and Dibenzo[d,f][1,3]diazepines. -Quinazolines (VII), perimidines (V) and dibenzodiazepines (III) are efficiently prepared by reacting thioanilides (I) with aromatic diamines. In the case of amines (II) and (IV), non-ionic systems are obtained because of the lower basicity of the aromatic amino groups compared to amine (VI). -(ZALESKA*, B.; KARELUS, M.; TRZEWIK, B.; SERDA, P.; J. Chem. Res. 2007, 4, 195-199; Dep. Org. Chem., Jagiellonian Univ., PL-30-060 Krakow, Pol.; Eng.) -R. Langenstrassen 42-165

Syntheses of novel diaryl[d,f ][1,3]diazepines via one-pot Suzuki coupling followed by direct ring closure with carboxylic acids

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et al. 2012

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A series of novel and diverse diaryl[d,f][1,3]diazepines were designed and synthesized to expand the pharmaceutical utility of the [6,7]bicyclic molecular skeletons. The facile synthesis involved two key steps: a one-pot Suzuki coupling to construct the bi-aryl intermediates from corresponding halides, and a ring closure by direct condensation with carboxylic acids.

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