Improved fischer indole reaction for the preparation of N, N-dimethyltryptamines: synthesis of L-695,894, a potent 5-HT1D receptor agonist

…, RD Larsen, TR Verhoeven, PJ Reider

Index: Chen; Senanayake; Bill; Larsen; Verhoeven; Reider Journal of Organic Chemistry, 1994 , vol. 59, # 13 p. 3738 - 3741

Full Text: HTML

Citation Number: 142

Abstract

Traditional syntheses ofN, N-dimethyltryptamines use a two-step procedure: a Fischer indole reaction4 between a hydrazines and the acetal 66 to construct the heterocycle, followed by a reductive alkylation ofthe resultant primary amine. There are major shortcomings with this sequence for the synthesis of L-695,894 (Scheme 1): First, the side chain precursor 4- chlorobutane dimethyl acetal (6) neces-

Related Articles:

Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus

[Qu, Shi-Jin; Wang, Gui-Feng; Duan, Wen-Hu; Yao, Shan-Yan; Zuo, Jian-Ping; Tan, Chang-Heng; Zhu, Da-Yuan Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 10 p. 3120 - 3127]

Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (. ident. Polyfibrospongia) echina

[Djura; Stierle; Sullivan; et al. Journal of Organic Chemistry, 1980 , vol. 45, # 8 p. 1435 - 1441]

Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (. ident. Polyfibrospongia) echina

[Djura; Stierle; Sullivan; et al. Journal of Organic Chemistry, 1980 , vol. 45, # 8 p. 1435 - 1441]

Synthesis of Functionalized Indole??and Benzo??Fused Heterocyclic Derivatives through Anionic Benzyne Cyclization

[Chemistry - A European Journal, , vol. 8, # 9 p. 2034 - 2046]

Synthesis of Functionalized Indole??and Benzo??Fused Heterocyclic Derivatives through Anionic Benzyne Cyclization

[Chemistry - A European Journal, , vol. 8, # 9 p. 2034 - 2046]

More Articles...