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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 1
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Original Articles

Cheap and Efficient Protocol for the Synthesis of Tetrahydroquinazolinone, Dihydropyrimidinone, and Pyrimidinone Derivatives

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Pages 8-20 | Received 19 Aug 2008, Published online: 09 Dec 2009
 

Abstract

The article reports a practical, simple, and inexpensive procedure for the synthesis of tetrahydroquinazolinone and dihydropyrimidinone derivatives from aldehydes, cyclic ketones, and urea using a catalytic amount of ammonium chloride or lithium perchlorate. The protocol provides good yields and simple workup procedure for the products. By this method, we have prepared and characterized the 4-aryl-3,4,5,6-tetrahydrobenzo[h]quinazolin-2(1H)-one (3a, c, d, f, g, j, k), 4-aryl-3,4-dihydro-1H-indeno[1,2-d]pyrimidin-2(5H)-one (3b, e, h, i), 4-aryl-5,6-dihydrobenzo[h]quinazolin-2(3H)-one (3j′, k′, l′), and 4-aryl-3,5-dihydro-2H-indeno[1,2-d]pyrimidin-2-one (3i′, m′, n′, o′, p′) derivatives. Furthermore, we have synthesized the pyrimidinone derivatives (6a′–e′) using a catalytic amount of cupric chloride from aldehydes, acyclic ketones and urea. The tautomeric interconversion of pyrimidinone derivatives 6a′–e′ ↔ 6a″–e″ has been observed.

Notes

a Reaction conditions: aldehyde 2 mmol, α-tetralone or 1-indanone 2 mmol, urea 3 mmol, TMSCl 2 mmol, NH4Cl 50 mol% or LiClO4 20% w/w aldehyde, 10 mL CH3CN, reflux 6h.

b The number between the parentheses shows the ratio of the nonoxidized to oxidized products.

c Isolated yield using NH4Cl catalyst; the number between the parentheses shows the yield using LiClO4 catalyst.

a Reaction conditions: aldehyde 2 mmol, acetophenone or 4-methoxy acetophenone 2 mmol, urea 3 mmol, TMSCl 2 mmol, CuCl2 10 mol%, 10 mL CH3CN, reflux 8 h.

b Isolated yield.

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