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Chemo‐ and diastereoselective synthesis of new oxa[3.3.3]propellane via a domino cascade four‐component reaction based on diketene
Author(s) -
Rezvanian Atieh,
Salimi Mehri,
Zadsirjan Vahideh,
Mahmoodi Fahame,
Heravi Majid M.
Publication year - 2020
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.4126
Subject(s) - chemistry , diketene , cascade reaction , malononitrile , knoevenagel condensation , propellane , intramolecular force , domino , combinatorial chemistry , tautomer , organic chemistry , triethylamine , catalysis , bicyclic molecule
A highly convergent, eco‐friendly and straightforward synthesis of new O ‐fused heterocycles, functionalized indeno[1,2‐ b ]furan derivatives was successfully accomplished through a one‐pot four‐component cascade reaction involving, ninhydrin, malononitrile, diketene and various primary amines in the presence of a catalytic quantity of triethylamine in ethanol at ambient temperature, in one pot fashion. This new efficient cascade reaction generates two rings by the simultaneous construction of C‐N (one), C‐O (two) and C‐C (two) multiple bonds, presumably through a sequence of Knoevenagel reaction/Michael addition/intramolecular O ‐cyclization and imine‐enamine/keto‐enol tautomerization. The merits of this protocol are highlighted as utilization of inexpensive commercially accessible starting materials, operational simplicity, atom economy, clean reaction profile, simple work‐up procedure being conducted at ambient temperature in relatively short reaction times, preventing chromatographic purification, giving excellent yields, and tolerance to a wide variety of functional groups.