79444-94-3

Upstream product

• 1021178-39-1 4-chloro-1-methoxy-1,3-bis-(trimethylsilyloxy)buta-1,3-diene 
• 57155-06-3 (Z)-4-methoxybut-3-en-2-one 
• 4652-27-1 4-methoxy-3-buten-2-one 
• 33528-09-5 methyl 6-methylsalicylate 

Downstream Products

• 13113-26-3 3-chloro-2-methoxy-6-methylbenzoic acid 
• 79444-95-4 methyl 3-chloro-6-methyl-O-carboxymethylsalicylate 

Relevant academic research and scientific papers

Synthetic studies toward inducamide C

The alkaloid inducamide C is proposed to contain a very rare benzoxazepine ring. Herein, we report that the benzoxazepine ring in inducamide C is unstable and prone to rearrangement, indicating that structural revision of the natural product may be necessary. In a first-generation synthetic approach, attempts to assemble the benzoxazepine by cyclization of 4-hydroxyinducamide A led to the regioisomeric oxepanoindole, a result of the 4-hydroxyindole (C4-OH) undergoing preferential cyclization instead of the desired chlorosalicylic acid C15-OH. A second-generation approach involved dealkylation of O-isopropylinducamide C, but the same oxepanoindole formed via rearrangement of the proposed inducamide C structure. Computational studies validate preferential formation of the oxepanoindole and the lactone in O-isopropylinducamide C is susceptible to nucleophilic attack. Thus, inducamide C is either highly unstable or in need of structural revision. This journal is

Diversity-oriented synthesis of chlorinated arenes by one-pot cyclizations of 4-chloro-1,3-bis(trimethylsilyloxy)buta-1,3-dienes

A variety of 3-chlorosalicylates were prepared by one-pot cyclizations of the first reported 4-chloro-1,3-bis(trimethylsilyloxy)buta-1,3-dienes with various 1,3-dielectrophiles, These include cyclizations with 3-silyloxy-2-en-1-ones, 3-aryl-3-silyloxy-2-en-1-ones, 1-methoxy-1-en-3-ones, 1,1-bis-(methylthio)-1-en-3-ones, 3-oxo orthoesters, 1,1,3,3- tetraethoxypropanes, 1,1-diacetylcyclopropane, and 3-formylchromones.

The first 4-chloro-1,3-bis(trimethylsilyloxy)-1,3-diene and its application to the regioselective synthesis of chlorinated arenes

Chlorinated phenols, benzophenones, and butenolides are prepared by various one-pot cyclization reactions of the first 4-chloro-1,3-bis(trimethylsilyloxy)-1,3-butadiene.