✦ LIBER ✦

Simultaneous Formation of 8H-Isoquino[2,1-b][2,7]naphthyridin-8-ones and 13H-Pyrido[4′,3′:3,4]pyrrolo[2,1-b][3]benzazepin-13-ones, a Novel Potential Alkaloidal System

✍ Scribed by Kuppuswamy Nagarajan; Patrick J. Rodrigues; Munirathinam Nethaji; Markus Vöhler; Wolfgang von Philipsborn

Publisher: John Wiley and Sons
Year: 1994
Tongue: German
Weight: 473 KB
Volume: 77
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19940770118

No coin nor oath required. For personal study only.

✦ Synopsis

190, CH-8057 Zurich (26. VIII. 93) Condensation of 3,4-dihydro-6,7-dimethoxyisoquinoline (4) with 4-methylnicotinoyl chloride (12) in refluxing pyridine gives 5,6,13,13a-tetrahydro-2,3-dimethoxy-8~-isoquino[2,l-b][2,7]naphthyridin-8-one (Il), along with some of its 13,13a-didehydro derivative 7. A similar reaction of 4 with 4-(chloromethyl)nicotinoyl chloride (14) affords, in addition to 7, the isomeric product 10,l l-dihydro-7,8-dimethoxy-13H-pyrido[4',3':3,4]pyrrolo[2,lb][3]benzazepin-13-one (3). Analogous pairs of products are obtained from 3,4-dihydro-6,7-(methylenedioxy)-and 3,4-dihydro-6,7,8-trimethoxy-isoquinolines (15 and 18, resp.). The structure of 3 was established by extensive NMR data and confirmed by single-crystal X-ray studies. Structure 7 has the ring system of the Alangium alkaloids like alangimarine (l), while the isomeric ring system 3 is predicted to be present in nature on biogenetic reasoning.

📜 SIMILAR VOLUMES

Synthesis of Some Novel Azetidino[2,3-b]

Synthesis of Some Novel Azetidino[2,3-b][1,8]naphthyridin-2(1H)-ones and 1,2,4-Triazolo[4,3-a][1,8]naphthyridines.

✍ K. Mogilaiah; P. Raghotham Reddy; R. Babu Rao; N. Vasudeva Reddy 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 104 KB 👁 1 views

New Synthesis of 1,2,3,6,7,11b-Hexahydro

New Synthesis of 1,2,3,6,7,11b-Hexahydro-4H-pyrimido[6,1-a]isoquinolin-4-ones and 2,3,6,7,12,12b-Hexahydropyrimido[1′,6′:1,2]pyrido [3,4-b]indol-4(1H)-ones.

✍ Alexander S. Fisyuk; Alexei Yu. Mukanov; Elena Yu. Novikova 📂 Article 📅 2004 🏛 John Wiley and Sons ⚖ 94 KB 👁 1 views

Synthesis of 15H-Isoquino[2′,3′:3,4]imid

Synthesis of 15H-Isoquino[2′,3′:3,4]imidazo[2,1-b]quinazoline-7,13,15-triones and 14H-isoquino[2′,3′:3,4]imidazo[2,1-b]benzo[g]quinazoline-8,14,16-trione as New Polycyclic Fused-Ring Systems.

✍ Ahmed I. Khodair; Jean-Pierre Gesson; El-Sayed H. El-Ashry 📂 Article 📅 2005 🏛 John Wiley and Sons ⚖ 25 KB 👁 1 views

Protoberberine aus Reissert-Verbindungen

Protoberberine aus Reissert-Verbindungen, 3. Mitt.: Synthese und Umsetzungsversuche von 8H-Isochino [2,1-b][2,7]naphthyridin-8-on. Protoberberines from Reissert Compounds, III: Synthesis and Attempted Reactions of 8H-Isoquino[2,1-b][2,7]naphthyridin-8-one

✍ Eberhard Reimann; Helmut Benend 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 279 KB 👁 2 views

Catalytic hydrogenation of 3-benzyloxyca

Catalytic hydrogenation of 3-benzyloxycarbonylaminoazino[1,2-x]-azin-4-ones. A facile access to 3-amino-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyridin-4-ones and 3-Amino-6,7,8,9-tetrahydro-4H-azino[1,2-x]pyrimidin-4-ones

✍ Simon Rečnik; Renata Toplak; Jurij Svete; Lucija Pizzioli; Branko Stanovnik 📂 Article 📅 2000 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 615 KB

## Abstract By catalytic hydrogenation of 3‐(benzyloxycarbonyl)amino‐4__H__‐pyrido[1,2‐__a__]pyridin‐4‐ones **28** and **29**, and azino[1,2‐__x__]pyrimidin‐4‐ones **32–35, 41**, and **42**, partial saturation of the heterocyclic systems and removal of the benzyloxycarbonyl moiety was observed to g

Synthesis of 6,7,8,9-tetrahydropyrido[2,

Synthesis of 6,7,8,9-tetrahydropyrido[2,3-b]indolizine and 3,4-dihydro-2H-pyrido[2′,3′:4,5]pyrrolo[2,1-b][1,3]oxazine derivatives as new melatonin receptor ligands

✍ Hervé Van de Poël; Gérald Guillaumet; Marie-Claude Viaud-Massuard 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 216 KB

The synthesis of new tricyclic azaindolic analogs of the hormone melatonin is described. Treatment of 1-(4-bromobutyl)pyrrolo[3,2-b]pyridine derivative with tributyltin hydride and AIBN results in radical cyclisation to give the 6,7,8,9-tetrahydropyrido[2,3-b]indolizine ring system. A new synthetic