Contrasting Responses of Pyrido[2,1-a]isoindol-6-ones and Their Sultam Counterparts to Photochemical Activation

• Published in: Journal of organic chemistry Vol. 74; no. 5; pp. 1982 - 1987
• Main Authors: Paquette, Leo A, Dura, Robert D, Modolo, Isabelle
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.03.2009; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Cyclization; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Isoindoles - chemical synthesis; Isoindoles - chemistry; Molecular Structure; Organic chemistry; Photochemistry; Physical chemistry of induced reactions (with radiations, particles and ultrasonics); Physical Sciences; Preparations and properties; Pyridines - chemical synthesis; Pyridines - chemistry; Science & Technology; Stereoisomerism; Sulfanilamides - chemistry; SULFOXIDES; YNAMIDES; MIYAURA DOMINO REACTIONS; BICYCLIC SULTAM; THIENOPYRIDINES; TRICYCLIC SYSTEMS; CHEMISTRY; SULFONES; N-OXIDES; SELECTIVE FORMATION; Sulfur nitrogen heterocycle; Sigmatropic reaction; Regioselectivity; Nitrogen heterocycle; Lactam; Metathesis; Polymerization; Selectivity; Photochemical reaction; Allylic compound; Ring cleavage; Imide; Saccharin; Side chain; Sultam; Cyclization; Conjugated dienic compound; Irradiation; Dimer; Chemical synthesis; Dimerization; Sensitizer; Acetone; Excited state

A ring-closing metathesis-based strategy has allowed access to an unreported pair of pyridoisoindolones and their previously unknown sultam counterparts. The synthetic routing takes advantage of the ready availability of N-allylphthalimide and N-allylsaccharin and proceeds via the proper incorporati...