✦ LIBER ✦

Synthesis of substituted 3-amino-4-cyano-1-oxo-1,2,5,10-tetrahydroazepino [3,4-b]indoles

✍ Scribed by Reinhard Troschütz; Annin Hoffmann

Publisher: Journal of Heterocyclic Chemistry
Year: 1997
Tongue: English
Weight: 830 KB
Volume: 34
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570340510

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The preparation of 3‐amino‐ and 3‐dialkylamino‐4‐cyanoazepino[3,4‐fc]indoles bearing substituents on the aromatic nucleus and N^10^ is outlined. Starting from suitable substituted ethyl 3‐formylindole‐2‐carboxy‐latcs 2, condensation with malononitrile (3) and subsequent sodium borohydride‐reduction yielded ethyl 3‐(2,2‐dicyanoethyl)indole‐2‐carboxylates 5 and 19, respectively, which were cyclized in boiling alkoxides to 3‐alkoxy‐4‐cyanoazepino[3,4‐b]indoles 10,11,20 and 21. This sequence constitutes a novel and flexible route to functional azepino[3,4‐b>]indoles. The aminolysis of 10,11,20 and 21 with different amines and ammonia yielded the title compounds which were screened for their possible biological activity.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of Substi

ChemInform Abstract: Synthesis of Substituted 3-Amino-4-cyano-1-oxo-1,2,5,10-tetrahydroazepino[3,4-b]indoles.

✍ R. TROSCHUETZ; A. HOFFMANN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

Synthesis of 4-Substituted Azepino[3,4-b

Synthesis of 4-Substituted Azepino[3,4-b]indole-1,5-diones.

✍ Julien Perron; Benoit Joseph; Jean-Yves Merour 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 121 KB 👁 1 views

Synthesis of novel fluorine-containing t

Synthesis of novel fluorine-containing tetracyclic ring systems: 2-Methyl-1-oxo-11H-1,2,4-triazino [3′,4′:3,4][1,2,4] triazino [5,6-b] indole and 3-methyl-4-oxo- 11H-1,2,4-triazino [4′,3′: 2,3][1,2,4] triazino [5,6-b] indole

✍ KrishnaC. Joshi; Pooran Chand; Anshu Dandia; Nidhal Ahmed 📂 Article 📅 1987 🏛 Elsevier Science 🌐 English ⚖ 38 KB

One-Step Synthesis of 5-Acetyl-2-amino-4

One-Step Synthesis of 5-Acetyl-2-amino-4-aryl-3-cyano-4H-pyrano[3,2-b]indoles. Molecular and Crystal Structure of 5-Acetyl-2-amino-4-(4′-chloro-3′-nitrophenyl)-3-cyano-4H-pyrano [3,2-b]indole.

✍ A. M. Shestopalov; O. A. Naumov; V. N. Nesterov 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 95 KB 👁 1 views

Synthesis of Substituted Azepino[3,4-b]i

Synthesis of Substituted Azepino[3,4-b]indole-1,5-diones.

✍ Julien Perron; Benoit Joseph; Jean-Yves Merour 📂 Article 📅 2005 🏛 John Wiley and Sons ⚖ 15 KB 👁 1 views

Synthesis of Substituted Azepino[3,4-b]i

Synthesis of Substituted Azepino[3,4-b]indole-1,5-diones

✍ Julien Perron; Benoît Joseph; Jean-Yves Mérour 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 English ⚖ 164 KB

## Abstract Cyclic β‐amino esters **4**, obtained from lactams, were condensed with indole‐2‐carbonyl chloride to afford the corresponding amides. Similarly, unusual conditions led to cyclisation at the 3‐position of the indole moiety in the presence of __p__TSA and ethylene glycol to afford previo