Tandem rearrangement involving a β-hydroxysulfoxide and cyclization processes toward the 1-benzenesulfonyl-5-benzenethio-1,2,2a,3,4,5-hexahydrobenz[c,d]indole oxygenated at the 4-position

Author:

Stamos Ioannis K.

Publisher

Wiley

Subject

Organic Chemistry

Reference16 articles.

1. The potential utility of homoacylation through the pummerer rearrangement-intermediates. A direct approach to the 1-benzene-sulfonyl-4-keto-8-methoxy-1,2,2a,3,4,5-hexahydrobenz-[cd]indoleviaintra-homoacylation

2. Action of Metal Hydrides on β-(3-Indolyl)ethyl-1-pyridinium Salts*1,2

3. When for the preparation of benzenesulfinylmethyl lithium was used lithium dialkylamines as bases, generated in situ from n-butyl-lithium and a secondary amine such as diethylamine, the yield of compound 3 was higher most of the times.

4. AN IMPROVED SYNTHESIS OF 1-BENZOYL-4-KETO-1,2,2A,3,4,5-HEXAHYDROBENZ [cd]INDOLE

5. The procedure which was followed is that described in ref 1 for the methoxy analogue. The product was a white solid consisting of two diastereomers, in 81% yield having a melting range of mp 137-147°. One of the diastereomers, isolated accidentally during the purification procedure by chromatography on silica gel (ethyl acetate with a small amount of ethanol) and then recrystallization from ethyl acetate-dichlo-romethane, had mp 149-151°.

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