A Simple Synthesis of 5-Spirobarbituric Acids and Transformations of Spirocyclopropanobarbiturates...

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2006 Barbituric acid derivatives R 0530 A Simple Synthesis of 5-Spirobarbituric Acids and Transformations of Spirocy- clopropanobarbiturates to 5-Substituted Barbiturates. — Reaction of barbituric acids (I) with dihaloalkanes under phase-transfer catalysis conditions provides access to 5-spirobarbituric acid derivatives in moderate to good yield. The spiro[2.5]barbituric acid (IIIa) undergoes ring-opening reactions with nucleophiles as well as electrophiles to furnish respective C-5 substituted barbituric acids. — (SINGH*, P.; PAUL, K.; Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 45 (2006) 1, 247-251; Dep. Chem., Guru Nanak Dev Univ., Amritsar 143 005, India; Eng.) — A. Forchert 18- 154

Transcript of A Simple Synthesis of 5-Spirobarbituric Acids and Transformations of Spirocyclopropanobarbiturates...

Page 1: A Simple Synthesis of 5-Spirobarbituric Acids and Transformations of Spirocyclopropanobarbiturates to 5-Substituted Barbiturates.

2006

Barbituric acid derivativesR 0530 A Simple Synthesis of 5-Spirobarbituric Acids and Transformations of Spirocy-

clopropanobarbiturates to 5-Substituted Barbiturates. — Reaction of barbituric acids (I) with dihaloalkanes under phase-transfer catalysis conditions provides access to 5-spirobarbituric acid derivatives in moderate to good yield. The spiro[2.5]barbituric acid (IIIa) undergoes ring-opening reactions with nucleophiles as well as electrophiles to furnish respective C-5 substituted barbituric acids. — (SINGH*, P.; PAUL, K.; Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 45 (2006) 1, 247-251; Dep. Chem., Guru Nanak Dev Univ., Amritsar 143 005, India; Eng.) — A. Forchert

18- 154