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A Concise and Efficient Concurrent Synthesis of 6,11-dihydrodibenzo[b,e]azepines and 5,6,11,12-tetrahydrodibenzo[b,f]azocines and Their Conversion to 4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylates and N-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocines: Synthetic Sequence, Spectroscopic Characterization and the Structures of Two Products

A Concise and Efficient Concurrent Synthesis of 6,11-dihydrodibenzo[b,e]azepines and 5,6,11,12-tetrahydrodibenzo[b,f]azocines and Their Conversion to 4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylates and N-acetyl-5,6,11,12-tetrahydrodibenzo[b,f]azocines: Synthetic Sequence, Spectroscopic Characterization and the Structures of Two Products

Lina M Acosta Quintero, Alirio Palma, Justo Cobo, Christopher Glidewell

Acta Crystallogr C Struct Chem. 2019 Jun 1;75(Pt 6):650-656.

PMID: 31166916

Abstract:

Reaction of 2-allyl-N-benzyl-4-fluoroaniline or 2-allyl-N-benzyl-4-chloroaniline with 98% sulfuric acid leads to the concurrent formation of halogeno-substituted 11-ethyl-6,11-dihydrodibenzo[b,e]azepines, (II), and halogeno-substituted 11-methyl-5,6,11,12-tetrahydrodibenzo[b,f]azocines, (III), in each case in (II):(III) molar ratios of ca 2:1. Further reaction of (II) leads to ethyl 13-ethyl-2-halogeno-4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylate, while acetylation of (III) gives the corresponding N-acetyl derivatives. The dibenzo[b,e]azepine and dibenzo[b,f]azocine ring systems are of importance in forming the core of a variety of bioactive compounds. In ethyl 13-ethyl-2-fluoro-4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylate, C22H20FNO3, (IVa), the azepine ring adopts a conformation close to the twist-boat form, and the molecules are linked into a three-dimensional framework structure by a combination of C-H...O and C-H...π(arene) hydrogen bonds. The azocine ring in 5-acetyl-2-chloro-11-methyl-5,6,11,12-tetrahydrobenzo[b,f]azocine, C18H18ClNO, (Vb), adopts the boat-boat conformation and the molecules are again linked by C-H...O and C-H...π(arene) hydrogen bonds, but this time form a sheet structure.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP668983979	Dibenzo[b,d]thien-2-ylboronic acid		668983-97-9	Price

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