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Photochemistry of the Phthalimide System, 39. Photoinduced Reactions, 84. Photochemistry of ω‐Phthalimidoalkanoic Acid Derivatives Syntheses of Multicyclic Fused Hydropyrazines and 1,4‐Diazepines
Author(s) -
Takechi Haruko,
Machida Minoru,
Kanaoka Yuichi
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619860506
Subject(s) - chemistry , phthalimides , thioester , phthalimide , imide , moiety , amide , photochemistry , decarbonylation , alkyl , organic chemistry , catalysis , enzyme
Photochemical reactions of phthalimides having various carbonyl functions (amides 3a – h , esters 11, 14 , and thioester 17 ) in their N ‐alkyl side chain are studied. By irradiation fused hydropyrazines ( 4a, e, g, h ) and hydro‐1,4‐diazepines ( 4b, f ) were formed from amide derivatives 3 through photocyclization, whereas the esters 11, 14 showed addition and reduction reactions of the imide carbonyl group, and thioester 17 showed Norrish‐type I reaction of the thioester moiety, in each case, however, without yielding cyclized products.