Chlorotrimethylsilane-promoted one-pot synthesis of steroidal[17,16-d]pyrimidines.
A novel and practical procedure was developed for the preparation of steroidal[17,16-d]pyrimidines by chlorotrimethylsilane (TMSCl)-promoted one-pot multicomponent Biginelli-like condensations of steroid-17-ones, urea and aromatic aldehydes. First, treatment of the steroid-17-ones with urea and aromatic aldehydes in dimethylformamide (DMF)/acetonitrile (ACN) gives the corresponding Biginelli products, following the aromatising reaction of the Biginelli products at the same time under air to yield the desired steroidal[17,16-d]pyrimidines (78-88%). Since steroidal[17,16-d]pyrimidines with hydroxyl group can be subsequently converted into steroidal[17,16-d]pyrimidine derivatives, this general method provides a highly efficient route to these biologically important compounds.
Wang
Cunde
C
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, Jiangsu, PR China. wangcd@yzu.edu.cn
Xu
Hangxian
H
Xie
Zengyang
Z
Wang
Xingbin
X
Zhang
Zonglei
Z
Sun
Qian
Q
D000447:Aldehydes / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry*; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*; D014508:Urea / Q000737:chemistry
D000447:Aldehydes; D011743:Pyrimidines; D013256:Steroids; D014297:Trimethylsilyl Compounds; C039293:trimethylchlorosilane; D014508:Urea