𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Electrophilic aromatic substitution of 3-alkoxy-6-alkyl-2-cyano-4,5,6a,11-tetraazabenzo[a]fluorene with orthoesters

✍ Scribed by Yoshihisa Okamoto; Yoshimi Yamaguchi; Mitsuaki Maeda; Yoshihisa Kurasawa

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
328 KB
Volume
45
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

magnified image

Fused tetracycles, 6‐alkyl‐3‐alkoxy‐2‐cyano‐4,5,6a,11‐tetraazabenzo[a]fluorene derivatives (5a,b,c,d,e,f), are synthesized from 2‐alkoxy‐5‐(benzimidazol‐2‐ylidene)‐3‐cyano‐6‐imino‐5,6‐dihydro‐pyridines (4b,c), and when refluxed in ethyl orthoacetate or ethyl orthopropionate, the elecrophilic aromatic substitution occurs at the ortho position of the cyanopyridine ring in the fused tetracycles (5b,c,e,f) to afford 6‐alkyl‐3‐alkoxy‐2‐cyano‐1‐ethyl‐4,5,6a,11‐tetraazabenzo[a]fluorenes(6b,c,e,f).

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis and Dimro
ChemInform Abstract: Synthesis and Dimroth Rearrangement of 6-Cyano-1,2,4-triazolo[4,3-a]pyrimidin-5- and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement.
✍ E. S. H. EL ASHRY; Y. EL KILANY; N. RASHED; A. MOUSAAD; H. ASSAFIR 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 1 views

Synthesis and Dimroth Rearrangement of 6-Cyano-1,2,4-triazolo[4,3a]pyrimidin-5-and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement. -Formic acid and triethyl orthoformate react with 2-hydrazinopyrimidin-4-ones (I) and (VI) to furnish triazo