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31.38 Product Class 38: Cyclic Arylamines

DOI: 10.1055/sos-SD-031-02143

Stevenson, P. J.Science of Synthesis, (2007311885.

General Introduction

The cyclic aromatic amines covered in this section are 7-azabicyclo[4.2.0]octa-1,3,5-triene {1, also called 7-azabicyclo[4.2.0]octa-1(6),2,4-triene, trivial name benzoazetine}, 2,3-dihydro-1H-indole (2, trivial name indoline), 1,2,3,4-tetrahydroquinoline (3), 2,3,4,5-tetrahydro-1H-1-benzazepine (4, also called 2,3,4,5-tetrahydro-1H-benzo[b]azepine), 1,2,3,4,5,6-hexahydro-1H-benzazocine (5, also called 1,2,3,4,5,6-hexahydrobenzo[b]azocine), 9,10-dihydroacridine (6, trivial name acridane), 10,11-dihydro-5H-dibenz[b,f]azepine (7, IUPAC name 10,11-dihydro-5H-dibenzo[b,f]azepine), 2,3-dihydro-1H-benzimidazole (8), 1,2,3,4-tetrahydroquinoxaline (9), 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (10, also called 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine), 5,6,11,12-tetrahydrodibenzo[b,f][1,4]diazocine (11), and 5,10-dihydrophenazine (12) (Scheme 1). Although cyclic arylamines have not been reviewed as a specific product class before, there are fairly comprehensive reviews on dihydroindoles,[‌1‌] tetrahydroquinolines,[‌2‌‌5‌] 10,11-dihydro-5H-dibenzo[b,f]azepines,[‌6‌] and 1,2,3,4-tetrahydroquinoxalines.[‌7‌] Some amides, carbamates, and tosylamides are also included in this section, where the functional group is bonded in an exocyclic manner to the heterocycle and from which the corresponding cyclic aromatic amine can, in principle, be released by hydrolysis. No examples are included where the corresponding groups are endocyclic and where a reduction would then be required to form the amine.

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References


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