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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 16
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Original Articles

SYNTHESIS OF NEW 3-SUBSTITUTED AND SPIRO 1,5-BENZODIAZEPIN-2-ONES UNDER PHASE-TRANSFER CATALYSIS CONDITIONS

Pages 2523-2535 | Received 10 Nov 2000, Published online: 09 Nov 2006
 

Abstract

1,3-Dihydro-4-phenyl-1,5-benzodiazepin-2-one 1 was treated with bromine in 1:1 molar ratio to get the corresponding 3-bromo derivative 2 which in turn reacted with different nucleophiles to get the corresponding 3-substituted derivatives 3–11. The cyclized compounds 4a , 5a , 7a,b , and 9a–c were achieved on refluxing compounds 4, 5, 6a,b , or 8 a–c respectively in diphenyl ether. Compound 1 was benzoylated with benzoyl chloride to give the corresponding 1-benzoyl derivative 12 which reacted with bromine in 1:2 molar ratio to yield the corresponding 3,3-dibromo derivative 13. Spiro benzodiazepines 14a–d–16 were obtained by reacting compound 13 with the proper bidentates. Compound 1 was treated with formaldehyde and secondary amines or thiols to give Mannich bases or sulphides 17–21, respectively.

Acknowledgments

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