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Synthesis of New Functionalized Heterocyclic [4,3,3] Propellanes via Three‐component Reaction Based on Ninhydrin–Phenol Adducts
Author(s) -
Sirouspour Mehdi,
Souri Sanaz
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2283
Subject(s) - chemistry , ninhydrin , adduct , furan , phenol , acetic acid , reactivity (psychology) , medicinal chemistry , organic chemistry , medicine , biochemistry , alternative medicine , amino acid , pathology
Three‐component reaction between ninhydrin–phenol adducts, dialkyl acetylenedicarboxylates, and triphenylphosphine was investigated. Utilizing this protocol, dialkyl 10‐oxo‐10 H ‐4b,9b‐(epoxyethanooxy)indeno[1,2‐ b ]benzofuran‐12,13‐dicarboxylates as functionalized heterocyclic [4,3,3] propellanes was synthesized in 6‐endo‐trig cyclization mode. 8‐hydroxyquinoline showed serendipitous reactivity and produced para substituted adduct in the reaction with ninhydrin in acetic acid media and hence produced dialkyl 8 a ‐(4‐(alkoxycarbonyl)‐2‐oxo‐2 H ‐pyrano[3,2‐ h ]quinolin‐6‐yl)‐8‐oxo‐8,8 a ‐dihydro‐2 H ‐indeno[2,1‐ b ]furan‐2,3‐dicarboxylate in the reaction with dialkyl acetylenedicarboxylates and PPh 3 .