3506-40-9

Upstream product

• 2298-49-9 N-methyl-3-oxo-N-(3-oxo-3-phenylpropyl)-3-phenylpropan-1-aminium chloride 
• 123-30-8 4-amino-phenol 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 3506-36-3 3-dimethylaminopropiophenone 
• 768-03-6 Phenyl vinyl ketone 
• 100-65-2 N-Phenylhydroxylamine 
• 96406-18-7 3-(N-hydroxy-anilino)-1-phenyl-propan-1-one 

Downstream Products

• 1120358-79-3 3,4,5,6-tetrahydro-4-(p-hydroxyphenyl)-2,7-diphenyl-2H-1,2,4-triazepine 
• 1325233-05-3 2-((dimethylamino)methyl)-4-(2,3,5,6-tetrahydro-2,7-diphenyl-1,2,4-triazepin-4-yl)phenol 
• 1325233-06-4 2,6-bis((dimethylamino)methyl)-4-(2,3,5,6-tetrahydro-2,7-diphenyl-1,2,4-triazepin-4-yl)phenol 
• 1325233-07-5 2,6-bis(piperidin-1-ylmethyl)-4-(2,3,5,6-tetrahydro-2,7-diphenyl-1,2,4-triazepin-4-yl)phenol 

Relevant academic research and scientific papers

Mannich bases as synthetic intermediates: Convenient synthesis of functionalized 1,2,4-triazepines, 1,4-diazepines and 1,5-diazocines

Transamination between the ketonic Mannich bases 1a, b and primary arylamines gave a series of ketonic sec-Mannich bases 2a - h. A variety of tetrahydro-1,2,4-triazepines 3a - f have been synthesized by treating the arylhydrazones of 2 with formaldehyde. A similar reaction with the benzenesulfonylhydrazone of 2b afforded 4. The 3-styryl-2H-1,2,4-triazepine 5 was obtained from the phenylhydrazone of 2a and cinnamaldehyde. Treatment of arylhydrazones of the 4-methoxystyryl keto base 7 with formaldehyde and cinnamaldehyde afforded the 3,4,5,6-tetrahydro-2H-1,2,4-triazepines 8a, b. Mannich reaction with 4-(p-hydroxyphenyl)-tetrahydro-1,2,4-triazepine 3d afforded the Mannich bases 9, 10 and 11. The reaction of 1b with o-phenylenediamine leads to the 1,5-benzodiazepine 13. The new tetrahydro- 1,4-diazepine and tetrahydro-1,5-diazocine Mannich bases 15 and 17 were obtained from 1b and ethylenediamine or 1,3-diaminopropane, respectively. The bi(piperidine) derivative 19 was obtained from 1a and 1,3-diaminopropane.

Mannich bases as synthetic intermediates: Alkylation of amines and diamines with bis-ketonic Mannich bases

The bis-ketonic Mannich base, N,N-bis(β-benzoylethyl)methylamine hydrochloride (1) reacts with primary arylamines and diamines to give ketonic sec-arylamines 3a-e and 4. The piperidines 7a-c were obtained from 1 and primary alkylamines, whereas the 1,4-diazepine derivative 10 was obtained from 1 and ethylenediamine. Treatment of the bis-base l,4-di[β-(N-morpholino) propionyl]benzene bis(hydrochloride) (11) with primary arylamines gave the corresponding bis-(sec-arylamines) 12a - b, whereas its reaction with o-phenylenediamine afforded the bis[1,5-benzodiazepine] ring system 14. The synthesis of the diazacyclophane ring system 15 has been achieved by treating 11 with piperazine. Attempted synthesis of 4-aza-[7]-paracyclophane (16) from 11 and benzylamine led to 17. The reaction of 1 or 11 with phenylhydrazine gave the 2-pyrazolines 18 and 19. Treatment of 3 or 4 with phenylhydrazine and formaldehyde afforded the 2H-1,2,4-triazepines 20a-c and the bis[2H-1,2,4-triazepine] ring system 21.