Premium
Nitrogen bridgehead compounds. Part 45 [1]. Synthesis of 6‐arylhydrazono‐6,7,8,9‐tetrahydro‐11 H ‐pyrido‐[2,1‐ b ]quinazolin‐11‐ones
Author(s) -
Kökösi József,
Szász György,
Hermecz István,
Podányi Benjámin,
Mészáros And Zoltan
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210512
Subject(s) - chemistry , methylene , solvent , medicinal chemistry , nuclear magnetic resonance spectroscopy , nitrogen , stereochemistry , organic chemistry
A series of 6‐arylhydrazono‐6,7,8,9‐tetrahydro‐11 H ‐pyrido[2,1‐ b ]quinazolin‐11‐ones 3–37 , conveneint starting materials for indolopyridoquinazolines, were prepared by diazonium coupling between aryldiazonium chlorides and 6,7,8,9‐tetrahydro‐ 2 , 6‐formyl‐5,7,8,9‐tetrahydro‐ 39 , 6‐(dimethylamino)methylene‐6,7,8,9‐ 38 or 6‐carboxyl‐5,7,8,9‐tetrahydro‐11 H ‐pyrido[2,1‐ b ]quinazolin‐11‐ones 43 . The arylhydrazono derivatives were also prepared from 6‐bromo‐ 45 or 6,6‐dibromo‐6,7,8,9‐tetrahydro‐11 H ‐pyrido[2,1‐ b ]quinazolines 46 with arylhydrazines. The structures of the 6‐arylhydrazonopyridoquinazolines were characterized by uv and 1 H nmr spectroscopy. The 6‐arylhydrazono derivatives show a solvent‐dependent E‐Z isomerism.