1414380-23-6

Basic information

• Product Name: 8,9-bis(phenylacetamide)-1,2,3,5,6,10a-hexahydropyrrolo[2,1-a]isoquinolin-3-one
• Synonyms: 8,9-bis(phenylacetamide)-1,2,3,5,6,10a-hexahydropyrrolo[2,1-a]isoquinolin-3-one
• CAS NO: 1414380-23-6
• Molecular Weight: 485.539
• Mol File: 1414380-23-6.mol

Chemical Properties

• CAS DataBase Reference: 8,9-bis(phenylacetamide)-1,2,3,5,6,10a-hexahydropyrrolo[2,1-a]isoquinolin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8,9-bis(phenylacetamide)-1,2,3,5,6,10a-hexahydropyrrolo[2,1-a]isoquinolin-3-one(1414380-23-6)
• EPA Substance Registry System: 8,9-bis(phenylacetamide)-1,2,3,5,6,10a-hexahydropyrrolo[2,1-a]isoquinolin-3-one(1414380-23-6)

Safety Data

• Hazardous Substances Data: 1414380-23-6(Hazardous Substances Data)

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 108163-97-9 ethyl N-(3,4-dimethoxyphenyl)ethyl-3-(aminocarbonyl)propionate 
• 33545-52-7 (+/-)-8,9-dimethoxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one 
• 724706-17-6 8,9-dihydroxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]-isoquinolin-3-one 
• 5326-87-4 N-(phenyl)bromoacetamide 
• 57231-75-1 ethyl 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propionate 

Relevant articles and documents

Synthesis of new antimicrobial pyrrolo[2,1-a]isoquinolin-3-ones

The attractive structure of the pyrroloisoquinoline moiety, together with its potential antimicrobial activity, encouraged us to prepare six 8-substituted and seven 8,9-disubstituted-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3- ones in a few steps with good yields. We applied a convenient methodology via double intramolecular cyclization conducted by a Bischler-Napieralski cyclodehydration-imine reduction sequence, which is widely employed in the synthesis of isoquinoline alkaloids. Therefore, we synthesized three series of these pyrrolo[2,1-a]isoquinolin-3-ones characterized by the substituent at the 8-position or 8,9-positions of the aromatic ring: (a) different side chains are attached to an 8-OH group (series 1); (b) a chlorine atom is attached to the 8-position (series 2); and (c) 8- and 9-carbons are bearing an identical group (series 3). The compounds bearing a benzylic moiety at the 8-position, for example, 8-benzyloxy-pyrrolo[2,1-a]isoquinolin-3-one (1a) and 8-(4-fluorobenzyloxy)-pyrrolo[2,1-a]isoquinolin-3-one (1e), as well as, a 8-chloro-9-methoxy moiety including the 8-chloro-9-methoxy-pyrrolo[2,1-a] isoquinolin-3-one (2a), provided the most fungicide and bactericide agents, respectively.