Detail of "2687-97-0"

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Facile synthesis of 7-10 membered rings by intramolecular condensation using dialkylcarbonate as solvent

Facile synthesis of 7-10 membered rings by intramolecular condensation using dialkylcarbonate as solvent. Ikemoto, Tomomi; Ito, Tatsuya; Nishiguchi, Atsuko; Tomimatsu, Kiminori (Chemical Development Laboratories, Takeda Pharmaceutical Company Limited, Yodogawa-ku, Osaka 532-8686, Japan). Tetrahedron Letters, 45(51), 9335-9339 (English) 2004 Elsevier B.V. CODEN: TELEAY. ISSN: 0040-4039. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) A convenient large-scalable synthesis of 1-benzazepines as an important intermediate of CCR5 antagonist, oral HIV-1 therapy, was established. The anilination of o-halogenobenzaldehydes with alkylamino-acids gave o-formylaniline-acids.In this article, certain chemicals are used. Some of their cas registry numbers are 2687-97-0 and 824951-30-6 The latter were esterified followed by an improved reaction using the combination of alcoholate and dialkyl carbonate in one-pot, to easily produce 1-benzazepines. E.g.,reaction of 2,5-FBrC6H3CHO with MeNHCH2CH2CH2CO2H.HCl led to the acid I, which was then esterified. Treating the esters with alcoholates in dialkyl carbonates gave 1-benzazepines II (R = Et, Me, H). Namely, these new processes afforded the desired product in only two steps from the starting materials, as compared with the previous 10 steps. Moreover, these convenient methodologies were applied to other heterocycles to give 8-10 membered rings, such as 1-benzazocine, 1-benzazonine, and 1-benzazecine. .