𝔖 Bobbio Scriptorium
✦   LIBER   ✦

New trans/cis tetrahydroisoquinolines. 2. trans- and cis-3-(1-methyl-1h-pyrrol-2-yl)-1-(2H)-oxo-2-phenethyl-1,2,3,4-tetrahydroisoquino-lin-4-carboxylic acids and subsequent transformations

✍ Scribed by M. P. Stoyanova; I. D. Kozekov; M. D. Palamareva

Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
98 KB
Volume
40
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Stereochemical course of the reaction of homophthalic anhydride and N‐(1‐methyl‐1__H__‐pyrrol‐2‐yl‐methylidene)‐phenethylamine was studied. Mixtures of the expected trans‐ and cis‐1,2,3,4‐tetrahydroiso‐quinoline‐4‐carboxylic acids trans‐4 and cis‐4 were obtained along with by‐products 5 and 6. The ratios of all products and the diastereomers, obtained under different reaction conditions, were established by pmr. THF as a solvent and ultrasonic treatment are applied for the first time in the reaction of this type. The reaction was made diastereoselective towards any isomer. The carboxylic group of trans‐4 was transformed in four steps into various cyclic amino‐methyl groups yielding numerous new tetrahydroisoquinolinones trans‐10a‐i incorporating a given fragment of pharmacological interest. Reduction of 10a‐i was studied.

📜 SIMILAR VOLUMES

New trans/cis tetrahydroisoquinolines. 1
New trans/cis tetrahydroisoquinolines. 1. trans-2-benzyl-3-(l-methyl-1h-pyrrol-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolin-1-ones and corresponding tetrahydroisoquinolines
✍ I. D. Kozekov; R. I. Koleva; M. D. Palamareva 📂 Article 📅 2002 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 82 KB

## Abstract The reaction of homophthalic anhydride and __N__‐(1‐methyl‐1__H__‐pyrrol‐2‐yl‐methylidene)‐benzylamine in boiling benzene afforded as a main product the expected substituted __trans__‐1,2,3,4‐tetrahydroisoquinoline‐4‐carboxylic acid **5**. The carboxylic group of **5** was transformed i

A simple and efficient synthesis of nove
A simple and efficient synthesis of novel N,N′-bis (1H-pyrrol-1-yl)-1-[2-(2-aryl-5-methyl-3-oxo-2,4-dihydro-3H-1,2,4-triazol-4-yl)ethyl]-1H-1,2,3-triazole-4,5-dicarboxamides
✍ Prashant R. Latthe; Vinay A. Sunagar; Bharati V. Badami 📂 Article 📅 2007 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 553 KB

## Abstract magnified image One‐pot reaction of 3‐aryl‐5‐methyl‐1,3,4‐oxadiazolin‐2‐ones **1a‐g** with ethanolamine yielded the 4‐(2‐hydroxyethyl)‐2‐aryl‐5‐methyl‐2,4‐dihydro‐3__H__‐1,2,4‐triazolin‐3‐ones **2a‐g** which were converted to the azido compounds **6a‐g**. These azides on 1,3‐dipolar cy