The Pictet-Spengler reaction of N(b)-hydroxytryptamines and cysteinals. II. Temperature effects, stereochemistry and mechanism

DOI: 10.1248/cpb.39.1672

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1672 - 1676 (1991)

Update date:2022-08-03

Topics:

Authors:

Liu Liu

Nakagawa

Ogata Ogata

Hino Hino

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1248/cpb.39.1672

The effect of temperature on the Pictet-Spengler reaction of N(b)-hydroxytryptamines (1) and cysteinals (2) has been examined. The optically active nitrones (3), obtained from 1 and 2, gave the corresponding N(b)-hydroxy-β-carbolines (4α and 4β) exclusively at -78°C in the presence of an excess of trifluoroacetic acid. The mechanism is discussed in relation to the stereochemistry.

Full text of DOI:10.1248/cpb.39.1672

NII-Electronic Library Service

Products guided by the article

Product name:C₂₄H₂₄Cl₃N₃O₅S

Cas No:136949-78-5

R&D Labs maybe for 136949-78-5

Chongqing Rong＆Quan Pharmaceutical Technology Co. , Ltd.

Contact:86-023-65268721

Address:No. 7, Manshanhong Village, Pingdingshan, Shapingba District, Chongqing Province, China
Foreschem Co., Ltd

Contact:+86-533-3112891

Address:zibo
Wuxi D-Stone International Co., Ltd.

Contact:+86-510-82740567

Address:21F Hengtong Int'l Centre, 215Zhongshan Road, Wuxi, Jiangsu,China
Chongqing KonAo Health Co.,Ltd

Contact:13687578375

Address:wuhan hubei china
Hangzhou yi lu biont technology Co., LTD

Contact:+86-571-88152630

Address:Hangzhoushi HuafengRoad Yicheng3Building1001room.

Relevant to this article

Design, synthesis and evaluation of novel thienopyrimidine-based agents bearing diaryl urea functionality as potential inhibitors of angiogenesis

Doi:10.1016/j.ejmech.2020.112942
(2021)
Ditopic receptors based on lower- and upper-rim substituted hexahomotrioxacalix[3]arenes: Cation-controlled hydrogen bonding of anion

Doi:10.1002/asia.201100926
(2012)
Rotational isomerism and fluxional behavior of bis(carbon dioxide) adducts of molybdenum

Doi:10.1021/ja00024a030
(1991)
A photoswitch based on self-assembled single microwire of a phenyleneethynylene macrocycle

Doi:10.1039/c0cc00739k
(2010)
Boron-based 4-hydroxytamoxifen bioisosteres for treatment of de novo tamoxifen resistant breast cancer

Doi:10.1021/ml3000287
(2012)
Green chemical approach: Microwave assisted, titanium dioxide nanoparticles catalyzed, convenient and efficient C-C bond formation in the synthesis of highly functionalized quinolines and quinolinones

Doi:10.1039/c4ra06772j
(2014)

Article Doi