65032-81-7Relevant academic research and scientific papers
Iminophosphorane-Mediated Synthesis of the Genotoxic Heterocyclic Amine Trp-P-2.
Molina, Pedro,Almendros, Pedro,Fresneda, Pilar M.
, p. 4701 - 4704 (2007/10/02)
A new eight-step synthesis of the genotoxic amine Trp-P-2 in an overall yield of 14.4 percent is described.The key step, formation of γ-carboline ring, involves a tandem aza Wittig/electrocyclic ring closure process.
Synthesis of Genotoxic Heterocyclic Amines Trp-P-1 and Trp-P-2
Hibino, Satoshi,Sugino, Eiichi,Kuwada, Takeshi,Ogura, Naoki,Sato, Kohichi,Choshi, Tominari
, p. 5917 - 5921 (2007/10/02)
Trp-P-1 (1a) and Trp-P-2 (1b) possessing a pyridoindole system have been newly synthesized.The key reaction step in the synthetic sequence has been the thermal electrocyclic reaction of the 1-azahexa-1,3,5-triene system 3 involving the indole bond derived from 2-vinylindoles 4. 2-Vinylindole 4a has been derived from N-(benzenesulfonyl)indole (5) in a four-step sequence. 2-Vinylindole 4b has been synthesized by two routes using either ethoxymethylidene Meldrum's acid (6b) or diethyl ethoxymethylidenemalonate (10) as Michael acceptors to the 2-lithio-N-(benzenesulfonyl)indole.
Synthesis of 3-Amino-5H-pyridoindoles, Carcinogenic γ-Carbolines
Akimoto, Hiroshi,Kawai, Akiyoshi,Nomura,Hiroaki
, p. 123 - 130 (2007/10/02)
The carcinogenic γ-carbolines 3-amino-1,4-dimethyl-5H-pyridoindole (1) and 3-amino-1-methyl-5H-pyridoindole (2) were synthesized efficiently by the following procedures.The key method involved the acid-catalyzed cyclization of 2-acetamido-3-(2-indolyl)alkanoic acids to 1,2-dihydro-γ-carbolines.This was followed by dehydrogenation to the γ-carbolinecarboxylates and conversion of the ester group to the carboxyl and finally to the amino one by Curtius rearrangement.Alternative methods involved the thermolysis of 4-(1-benzotriazolyl)-3,6-dimethyl-2-pyridinamine to synthesize 1 and the condensation of 3-acetylindole-2-acetonitrile with ammonia to synthesize 2.The structures of γ-carbolines 1 and 2 were unambiguously established by comparing samples of each synthesized by the two different routes.A selective and one-step synthesis of ethyl 2-acetamido-3-(2-indolyl)alkanoates was newly exploited starting from diethyl acetamidomalonate and quaternary ammonium salts of 2-indoles.
