Synthesis of 5-substituted and 5,6-disubstituted furo[2,3-d]pyrimidines from 2-methylthio-4,6-pyrimidindione and bifunctional electrophiles |
| |
Authors: | Gra?ina Petraityt? Vytenis Vaitkevi?ius Besra Özer Viktoras Masevi?ius |
| |
Affiliation: | 1. Department of Organic Chemistry, Faculty of Chemistry and Geosciences, Vilnius University, 24 Naugarduko Street, Vilnius, LT, Lithuania;2. Abant ?zzet Baysal University, Bolu, Turkey |
| |
Abstract: | A two-step protocol for the synthesis of 5-substituted or 5,6-disubstituted furo2,3-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 furo2,3-d]pyrimidines in moderate to good yields. |
| |
Keywords: | AEXCUJUYEZIWJV-UHFFFAOYSA-N ZNMXSHNBPYTVMD-UHFFFAOYSA-N PGKMWTAFZUKYBD-UHFFFAOYSA-N WOKSJZYCUXRVSZ-UHFFFAOYSA-N YIYSHCSJNSUWCO-UHFFFAOYSA-N YVFVTMASKVNALF-UHFFFAOYSA-N LIGACIXOYTUXAW-UHFFFAOYSA-N FKJSFKCZZIXQIP-UHFFFAOYSA-N KGHGZRVXCKCJGX-UHFFFAOYSA-N XQJAHBHCLXUGEP-UHFFFAOYSA-N SAIRZMWXVJEBMO-UHFFFAOYSA-N FNQGSOFXAPCRFY-UHFFFAOYSA-N RPHVWKCQQYMVFA-UHFFFAOYSA-N OVKFFZDZJMVSGM-UHFFFAOYSA-N HWTKKOHJYJQLEC-UHFFFAOYSA-N QZYLGYGYOPKTDV-UHFFFAOYSA-N YYPFFEMZLMPYLE-UHFFFAOYSA-N RSRXIKXAVHINNN-UHFFFAOYSA-N UQQGCPKOYCJZCW-UHFFFAOYSA-N SMFMUIOFDWQWOP-UHFFFAOYSA-N FAJIYZVKJMLNGF-UHFFFAOYSA-N ORTLYVUZDQZHTJ-UHFFFAOYSA-N ZDNXVWCAXCITSM-UHFFFAOYSA-N QZZPQFCUIDFOMJ-UHFFFAOYSA-N KYYVOUAQDHYIPQ-UHFFFAOYSA-N UIIQLGTWZREYIW-UHFFFAOYSA-N UGYXHUPZGWOOPI-UHFFFAOYSA-N XJRQFNYMOKZUNX-UHFFFAOYSA-N VJXAYXJEDQWLGG-UHFFFAOYSA-N Bifunctional electrophile Heterocycles Pyrimidines Cyclization Corresponding author |
本文献已被 ScienceDirect 等数据库收录! |
|