Ring Rearrangements and Reactivity of 3-((4-oxo-4H-chromen-3-yl)methylene)-4-phenyl-1H-[1,5]benzodiazepin-2(3H)-one Towards Some Nucleophiles

Hanan Salah; Eman Abdalla; Mohamed Hassan

doi:10.3390/ecsoc-18-a046

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Ring Rearrangements and Reactivity of 3-((4-oxo-4H-chromen-3-yl)methylene)-4-phenyl-1H-[1,5]benzodiazepin-2(3H)-one Towards Some Nucleophiles

Hanan Salah

¹,

Eman Abdalla

¹,

Mohamed M. Hassan

^{*

2}

¹ Chemistry Department, Faculty of Science, Sohag University, Egypt
² Chemistry Department, Faculty of Education, Ain Sham University, Cairo 11757, Egypt; Basic Science Department, Preparatory year deanship, Majmaah University, Amajmaah 11952, KSA

Published: 03 November 2014 by MDPI in The 18th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-18-a046

Abstract: Condensation of 4-phenyl-1H-[1,5]benzodiazepin-2(3H)-one (1) with 3-formylchromone (2) afforded a mixture of 3-(chromenylmethylene)-[1,5]benzodiazepinone 3 and 14-chromenylbenzodiazepino[2,3:6,5]pyrano[2,3-b]benzodiazepine 4. Ring rearrangements of compound 3 with different nucleophilic reagents, such as; potassium hydroxide and/or ammonium acetate led to rearrangement into pyranobenzodiazepine 5 and pyridobenzodiazepine 6, respectively. Treatment of compound 3 with hydrazine hydrate, hydroxylamine hydrochloride, malononitrile, cyanothioacetamide, 2-cyano-3,3-disufanylacrylonitrile, and/or 2-cyano-3-phenylamino-3-sufanylacrylonitrile, have been carried out at different conditions, leading to versatile heterocyclic substituted benzodiazepines at position 3, viz; pyrazole 8, isoxazole 9, pyridines 10 and 11, 1,3-dithiine 12, and 1,3-thiazine 13 derivatives.

Keywords: [1,5]Benzodiazepin-2(3H)-one; 3-formylchromone; nucleophilic reagents; ring rearrangement; heterocyclization

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