Tetrahedron

Synthesis and characterization of the aqueous solution chemistry of the food-derived carcinogen model N-acetoxy-N-(1-methyl-5H-pyrido [4, 5-b] indol-3-yl) acetamide …

S Rajagopal, ME Brooks, TM Nguyen, M Novak

Index: Rajagopal, Sridharan; Brooks, Michael E.; Nguyen, Thach-Mien; Novak, Michael Tetrahedron, 2003 , vol. 59, # 40 p. 8003 - 8010

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Citation Number: 12

Abstract

We report the synthesis of N-acetoxy-N-(1-methyl-5H-pyrido [4, 5-b] indol-3-yl) acetamide, 7, its N-pivaloyloxy analogue, 9, and improved synthesis of indole-2-acetonitrile, 3 (70% in five steps from indole-2-carboxylic acid), the carcinogenic amine Trp-P-2, 4 (40% from 3), and the nitro compound, 5 (40% from 4 by oxidation with H2O2 using Mo (CO) 6 catalyst). In aqueous solution at neutral pH, 7 primarily undergoes C–O bond cleavage to yield the ...