Preparation and thermal ring-closure of β-aryl vinyl carbodi-imides: synthesis of isoquinoline derivatives
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1727-1731
- https://doi.org/10.1039/p19900001727
Abstract
Reaction of the iminophosphoranes (7)–(9), derived from α-azidocinnamates and tri-phenylphosphine, with aromatic isocyanates gives either 1-arylaminoisoquinoline-3-carboxylates (10)–(12) or the corresponding carbodi-imides (14)–(18) which by thermal treatment at 230 °C are converted into 1-(N-aryl-N-imidazolylamino)isoquinoline-3-carboxylates (19)–(20). The iminophosphoranes (7) and (8) also react with aroyl chlorides to give the oxazolone derivatives (23)–(26).This publication has 10 references indexed in Scilit:
- Heterocyclization Reactions of Conjugated Heterocumulenes. Synthesis of Pyridine Derivatives by a Tandem Aza Wittig/Electrocyclization StrategyEuropean Journal of Inorganic Chemistry, 1989
- Conjugated carbodiimides: Preparation and thermal cyclization to 2-aminopyridine derivativesTetrahedron Letters, 1988
- Carbodiimide-mediated Annelation of a [1,2,4]Triazole Ring into a Heterocyclic Ring: Synthesis of [1,2,4]Triazolo[4,3-b]triazole, Imidazo[1,2-b][1,2,4]triazole and [1,2,4]Triazolo[1,5-d][1,2,4]triazine DerivativesHETEROCYCLES, 1988
- New heterocyclization reactions for the preparation of fused [1,2,4]triazoles: synthesis of 1,2,4-triazolo[4,3-b][1,2,4]triazole derivatives from 4-amino-1,2,4-triazoles and carbodi-imides or via iminophosphoranes and disubstituted thioureasJournal of the Chemical Society, Perkin Transactions 1, 1987
- [2,3] Fused indoles. Synthesis of β-carbolines and azepino[4,5-b]indoles from 3-(2-alkylindol-3-yl)-2-azidoacrylates1Journal of the Chemical Society, Perkin Transactions 1, 1984
- Formation of indoles, isoquinolines, and other fused pyridines from azidoacrylatesJournal of the Chemical Society, Perkin Transactions 1, 1984
- A Simple Preparation of 1,3-Dimethylisoquinoline and its DerivativesSynthesis, 1980
- Rearrangements in the pictet-gams isoquinoline synthesisTetrahedron Letters, 1977
- Geometric Isomers of 2-Aryl(Aralkyl)-4-arylidene(alkylidene)-5(4H)-oxazolonesSynthesis, 1975
- Zum Verhalten ungesättigter Ketoxime unter den Bedingungen der Beckmann‐Umlagerung, 3. Mitt.Archiv der Pharmazie, 1975