Synthesis of 5-substituted and 5,6-disubstituted furo[2,3-d]pyrimidines from 2-methylthio-4,6-pyrimidindione and bifunctional electrophiles
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Dosyalar
Tarih
2019
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Pergamon-Elsevier Science Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
A two-step protocol for the synthesis of 5-substituted or 5,6-disubstituted furo[2,3-d]pyrimidines using bifunctional electrophiles and a pyrimidine derivative was developed. The first step is O-alkylation of 2-methylthiopyrimidin-4,6-dione utilizing bifunctional electrophiles which are readily available from the corresponding ketones via bromination or oxidative mesylation procedures. The reaction furnishes 6-(2-oxoethoxy)pyrimidine derivatives in moderate yields, and the di-O-alkylated product, while still unavoidable under the proposed conditions, is easily removed upon recrystallization of the target compound. The second step is intramolecular cyclization of the mono O-alkylated pyrimidines on silica gel to give the target furo[2,3-d]pyrimidines in moderate to good yields. (C) 2019 Elsevier Ltd. All rights reserved.
Açıklama
Anahtar Kelimeler
O-alkylation, Bifunctional Electrophile, Heterocycles, Pyrimidines, Cyclization, Furo[2,3-d]pyrimidines
Kaynak
Tetrahedron Letters
WoS Q Değeri
Q2
Scopus Q Değeri
Q3
Cilt
60
Sayı
15
