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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 180, 2005 - Issue 11
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Original Articles

Regioselective Synthesis of 3-Benzylthiazolo[3,2-a]pyrimidones and 3-Benzyl-thiazolo[3,2-c]pyrimidones Through Palladium-Catalyzed Heteroannulation of Acetylenic Compounds

Majid M. Heravi Ferdowsi University of Mashhad, Iran and Azzahra University, Vanak, Tehran, Iran
,
Ali Kivanloo Ferdowsi University of Mashhad, Iran
,
Mohammad Rahimizadeh Ferdowsi University of Mashhad, Iran
,
Mehdi Bakavoli Ferdowsi University of Mashhad, Iran
,
Mitra Ghassemzadeh Chemistry and Chemical Engineering, Research Center of Iran, Tehran, Iran
&
Bernhard Neumüller Fachbereich Chemie der Philipps-Universität, Marburg, Germany
Pages 2407-2417 | Received 29 Apr 2004, Accepted 26 Oct 2004, Published online: 16 Aug 2006
 
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Abstract

The reaction of 2-(prop-2-ynylsulfanyl)pyrimidone 1 with various iodobenzenes in the presence of a palladium catalyst leads to regioselective cyclization to 3-benzylthiazolo [3,2-a] pyrimidones 3. The reaction of 4-(prop-2-ynylsulfanyl) pyrimidone 5 with various iodobenzenes in the same condition give the corresponding 3-benzylthiazolo[3,2-c]pyrimidones 6.

Notes

a w = 1/[σ2(F o )+ (0.0152 . P)2]; P = Max (F o 2, 0) + 2 · F c 2]/3.

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