Synthesis, X-Ray Crystal Structure, and Attempts to Cyclisize N-Alkylated-7-Glyoxyl-2,3-Diphenyl-4,6-Dimethoxyindoles  

Oleh:

Jumina

Jenis: Article from Journal - ilmiah nasional - tidak terakreditasi DIKTI
Dalam koleksi: SIGMA: Jurnal Sains dan teknologi vol. 10 no. 2 (Jul. 2007), page 111-117.
Topik: indole; glyoxylamide; glyoxyl ester; cyclisation; and pyrroloindole

Ketersediaan

Perpustakaan Pusat (Semanggi) Nomor Panggil: SS25.6 Non-tandon: 1 (dapat dipinjam: 0) Tandon: tidak ada

Lihat Detail Induk

Isi artikel

N-Indol-1-y!acetamide 3 was obtained in 90 % yield from treatment of 3,4-dimethoxy-2,3-diphenylindole 1 with N,N-dimethylchloroacetamide in dimethylsul¬foxide in the presence of potassium hydroxide. When reacted with oxalyl chloride in benzene followed by dimethylamine, indol-1-ylacetamide 2 turned to glyoxyla¬mide 3 in 89 % yield. Slighily different to this last phenomenon, indol-I-ylacetate 4 gave only 44 % of glyoxyl ester 5 when treated with oxalyl chloride in benzene, fol¬lowed by methanol. Both of glyoxylamide 3 and glyoxy! ester 5 failed to undergo cyclisation to generate the related pyrroloindoles when treated with some bases such as sodium hydride, sodium methoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The crystal structure of glyoxylamide 3 indicated that geometrically this glyoxylamide is unlikely to undergo cydilsation to afford the expected pyr¬roloindole.

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