A Facile Stereoselective Domino Approach for the Construction of Novel Bis(spiropiperidone)-Tetrahydrothiophene Hybrid Heterocycles

作者：Bharkavi Chelliah; Kumar Sundaravel Vivek; Perumal Subbu^*

来源：Synlett, 2015, 26(12): 1665-1670.

DOI：10.1055/s-0034-1380722

• domino reactions
• stereoselectivity
• (3E,5E)-3,5-bis(arylidene)-1-methyl/benzylpiperidin-4-ones
• 1,4-dithiane-2,5-diol
• bis(spiropiperidone)-tetrahydrothiophene hybrids

A library of novel bis-spiropiperidone-tetrahydrothiophene hybrid heterocycles have been synthesized via pseudo-three-component domino reaction of (3E,5E)-3,5-bis(arylidene)-1-methyl/benzyl piperidin-4-ones and 1,4-dithiane-2,5-diol in the presence of triethylamine. This transformation presumably proceeds via two annulations each involving the generation of 2-mercaptoacetaldehyde from 1,4-dithiane-2,5-diol-Michael addition-intramolecular aldol sequence which result in the creation of four new bonds in a one-pot operation. The advantages of this protocol are high atom economy, high stereoselectivity, short reaction time, and operational simplicity.

• 出版日期2015-7