Novel protocol for the synthesis of octahydropyrano- and thiopyrano[4,3-a]carbazole derivatives via Prins/Friedel-Crafts cyclization

作者：Reddy B V Subba^*; Reddy P Sivaramakrishna; Yadav J S; Sridhar B

来源：Tetrahedron Letters, 2013, 54(11): 1392-1396.

DOI：10.1016/j.tetlet.2012.12.113

• Prins/Friedel-Crafts reaction
• Acid catalysis
• Aldehydes
• Pyrano[4,3-a]carbazole

A novel Prins/Friedel-Crafts cyclization of (Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol with aldehydes has been achieved using a catalytic amount of BF3 center dot OEt2 under mild reaction conditions to produce the corresponding octahydropyrano[4,3-a]carbazole derivatives in good yields with high diastereoselectivity. The cross-coupling of (Z)-6-(1-methyl-1H-indo1-3-y1)hex-3-ene-1-thiol with aldehydes affords the corresponding octahydrothiopyrano[4,3-a]carbazole derivatives under similar conditions.

• 出版日期2013-3-13