Paper
One-pot Reaction of Mono and Dialdehydes with Unsymmetrical 1-methyl Barbituric Acid (1-MBA) and BrCN in the Presence of Triethylamine and L-(+)-tartaric Acid
- Authors:
- Nader Noroozi Pesyan; Mohammad Jalilzadeh
- Abstract
- One-pot reaction of unsymmetrical 1-methybarbituric acid (1-MBA), BrCN, mono- and dialdehydes in the presence of L-(+)-tartaric acid (L-(+)-TA) and/or triethylamine afforded diastereomeric mixtures of a series of stable heterocyclic mono- and bis-spiro barbiturates and their sulfur analogues which are dimeric forms of barbiturate (uracil and thiouracil derivative) at the range of 0°C to room temperature. The reaction of symmetrical (thio)barbituric acids with dialdehydes were afforded bis-spiro barbiturates instead, 1-MBA was afforded diastereomeric mixture of bis-spiro barbiturates under the same condition. Diastereoselectively reaction products in the presence of L-(+)-TA were also investigated. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR and Mass analyses. Mechanism of the formation is discussed.
- Keywords
- Diastereoselective; Unsymmetrical Barbituric Acid; Spiro[furo[2;3-d] Pyrimidine; BrCN; Uracil; Thiouracil; L-(+)-tartaric Acid
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