✦ LIBER ✦

Photochemical synthesis of 1,2,3,4-tetrahydroisoquinolin-3-ones from N-chloroacetylbenzylamines

✍ Scribed by Masaki Ikeda; Ken-ichi Hirao; Yohmei Okuno; Naganori Numao; Osamu Yonemitsu

Publisher: Elsevier Science
Year: 1977
Tongue: French
Weight: 793 KB
Volume: 33
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(77)80005-7

No coin nor oath required. For personal study only.

✦ Synopsis

When N-chloroacetyl-3-hydroxybenzylamine (37) in aqueous acetonitrile was irradiated, both ortho and para photocyclizations with reference to the OH group occurred to give 7-and 5 -hydroxy -3 -oxo -1,2,3,4tetrahydroisoquinolines ($2, 53). Similarly, 1 -methylisoquinoline derivatives (54, 55) were synthesized. N-Chloroacetyl -3,5 -dihydroxybenzylamine (39) gave a single photoproduct, 5,7 -dihydroxy -3 -oxo -1,2,3,4 -tetrahydroisoquinoline (56). These photocyclizations were smoothly extended to the synthesis of 1 -benzyl, 1 -(4'-methoxybenzyl)-and 1 -(3',4',5' -trimethoxybenzyl) -isoquinoline derivatives ($8-64).

MeO~

📜 SIMILAR VOLUMES

Chemically-enabled synthesis of 1,2,3,4-

Chemically-enabled synthesis of 1,2,3,4-tetrahydroisoquinolin-1-ones

✍ Paul S. Humphries; Gayatri Balan; Bruce M. Bechle; Edward L. Conn; Kenneth J. Di 📂 Article 📅 2009 🏛 Elsevier Science 🌐 French ⚖ 412 KB

We have developed a number of efficient protocols for the facile synthesis of 1,2,3,4-tetrahydroisoquinolin-1-ones. This synthetic methodology allowed concise and efficient exploration of the SAR in all areas of the molecule. A number of these methods proved to be versatile, efficient and amenable t

A convergent synthesis of 4-substituted

A convergent synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones

✍ Nathalie Cholleton; Samir Z. Zard 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 223 KB

ChemInform Abstract: A Convergent Synthe

ChemInform Abstract: A Convergent Synthesis of 4-Substituted 1,2,3,4-Tetrahydroisoquinolin-1-ones.

✍ N. CHOLLETON; S. Z. ZARD 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

Synthesis and κ binding affinity of 1-(p

Synthesis and κ binding affinity of 1-(pyrrolidin-1-ylmethyl)-2-(N-methyl)-4-[(3,4-dichloro)phenyl]-1,2,3,4 tetrahydroisoquinolin-3(2H)-ones

✍ GA Pinna; E Gavini; G Cignarella; S Scolastico; P Fadda 📂 Article 📅 1995 🏛 Elsevier Science 🌐 French ⚖ 513 KB

Synthesis of 1,3-Disubstituted N-Amino-1

Synthesis of 1,3-Disubstituted N-Amino-1,2,3,4-tetrahydroisoquinolines.

✍ Li Zhang; Xiu-Fang Zheng; Gregory Linn; Kang Zhao 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

Synthesis of 1,2,3,4-tetrahydroisoquinol

Synthesis of 1,2,3,4-tetrahydroisoquinolines from α-methyldopa

✍ Schneur Rachlin; Karin Worning; Jens Enemark 📂 Article 📅 1968 🏛 Elsevier Science 🌐 French ⚖ 168 KB