title: Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles.
abstract: The intramolecular 1,3-dipolar cycloaddition of isovanillin derived N-aryl hydroxylamines possessing ortho-allylic dipolarophiles affords novel benzo analogues of tricyclic isoxazolidines that can be readily transformed into functionalized lactams, γ-aminoalcohols and oxazepines. The corresponding N-unsubstituted hydroxylamines give rise to tetrahydroisoquinolines. Anxiogenic properties of these compounds are tested in zebra fish.
authors.affiliation: Dr Reddy's Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India. jiqbal@ilsresearch.org manojitpal@rediffmail.com neelimadt@ilsresearch.org.
authors.forename: Balakrishna
authors.initials: B
authors.lastname: Dulla
authors.forename: Neelima D
authors.initials: ND
authors.lastname: Tangellamudi
authors.forename: Sridhar
authors.initials: S
authors.lastname: Balasubramanian
authors.forename: Swapna
authors.initials: S
authors.lastname: Yellanki
authors.forename: Raghavender
authors.initials: R
authors.lastname: Medishetti
authors.forename: Rakesh
authors.initials: R
authors.lastname: Kumar Banote
authors.forename: Girish
authors.initials: G
authors.lastname: Hari Chaudhari
authors.forename: Pushkar
authors.initials: P
authors.lastname: Kulkarni
authors.forename: Javed
authors.initials: J
authors.lastname: Iqbal
authors.forename: Oliver
authors.initials: O
authors.lastname: Reiser
authors.forename: Manojit
authors.initials: M
authors.lastname: Pal
mesh_terms: D000818:Animals; D001007:Anxiety / Q000139:chemically induced*; D001547:Benzaldehydes / Q000737:chemistry*; D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006898:Hydroxylamines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009043:Motor Activity / Q000187:drug effects*; D015027:Zebrafish
chemical_list: D001547:Benzaldehydes; D006571:Heterocyclic Compounds; D006898:Hydroxylamines; C093382:isovanillin