Synthesis of novel 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolines via benzotriazole methodology (original) (raw)
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Synthesis of a Variety of Activated Pyrrolo[3,2,1-ij]quinolines
Synthesis, 2019
A range of 7,9-dimethoxypyrrolo[3,2.1-ij]quinolines have been prepared by the cyclisation of 7-formyl-1-diethylcarbethoxyindoles. The functionality at C5 has been varied by the conversion of the carbethoxy group into carboxy, azidocarbonyl and isocyanate groups. The hydroboration of a previously reported pyrroloquinolone gave a related 5-hydroxypyrrolo[3,2,1-ij]quinolone, and the hydroxyl group was sequentially converted into tosylate, azido and amino groups.
Tetrahedron, 1990
We now report a fundamentally new simple and apparently general method to the synthesis of fused pyrroles, namely, pyrrolo [ 1,2-alquinoxalines, indolo[3,2c]quinolines and indolo [ 1,2-c]quinazolines. Our approach is centered on the aza-Wittig type reaction of iminophosphoranes with heterocumulenes: e.g. isocyanates, isothiocyanates, carbon dioxide and carbon disulfide to give o-pyrrolylphenyl heterocumulenes 1, which subsequently undergo ring closure leading to the fused pyrroles 2 (Chart 1).
Synthesis of pyrrolo[1,2-c]quinazoline derivatives
Tetrahedron, 1992
Synthesis of pyrrolo[ 1 ,Zc]quinazoline derivatives 5361 Scheme 4 9:R=Me 1 O:R=OEt dOR I 12 :R=Me 13 :R=OEt 11 R2 R3 12.14 R' R2 R3 13 a Me H Synthesis of pyrrolo[l,Zc]quinazoline derivatives 5365 Column chromatography was performed on Merck Kieselgel 60, 0.063-0.2 mm and on Florisil 0.150-0.250 mm. Evaporation was carried out under vacuum in a rotary evaporator. Compounds 1 a7 and 1 b8 were prepared according to the literature procedure. Compounds Ga,b,e were prepared as previously reported 4. Ethyl 1-Acetyl-1,3-dihydro-2H-Indol-2-one-3-acetate 1 c. E-Ethyl 1-Acetyl-2H-indol-2-one-3-ylidene acetate 9 (2.5 g, 10 mmol) was dissolved in EtOAc (60 mL). 10% Pd/C (200 mg) was added and the mixture hydrogenated at r. 1. and atmospheric pressure; After 15 min the catalyst was filtered off and the solvent evaporated. Crystallization from Et20hexane gaves pure lc, 2.38 g (91 %), mp 79-80 "C.
2010
Reaction of aryl compounds containing primary amine with acetic anhydride gave the compound 1(a-f) and 4(af). Which on further treatment with Vilsmeier-Haack reagent (DMF+ POCl 3) gave the fused pyridine ring by cyclization, which gave compound 2-chloroquinoline-3-carbaldehyde 2a-f and 2-chloro-9H-pyrido [2,3-b]indole-3carbaldehyde 5a-f respectively. These compounds were containing the free aldehyde group in their structure which form schiff base on treatment with the different substituted aniline this was because off the presence of primary amine group. These compounds were containing quinoline (3a-f) and pyrido indole (6a-f) with schiff base (substituted-N-((2-chloroquinolin-3-yl) methylene)benzenamine 3a-f and substituted-N-((2-chloro-9Hpyrido[2,3-b]indol-3-yl) methylene)benzenamine 6a-f) which showed antimicrobial activity due to the presence of these potent groups in their structure.
Basic approaches to the synthesis of pyrrolo[1,2-a]quinolines derivatives: a review
Voprosy Khimii i Khimicheskoi Tekhnologii, 2019
At the present stage of the development of organic and bioorganic chemistry, several basic approaches to the synthesis of pyrrolo[1,2-a]quinolines are known. These compounds are of interest to the researches primarily as bioregulators with a wide spectrum of biological activity. This review is an attempt to systematize and generalize literary data relating to the chemistry of pyrrolo[1,2-a]quinoline and its derivatives as important synthetic substrates and precursors for the design of biologically active substances. The main approaches to the synthesis of these compounds, consisting in various preparative methods for constructing a tricyclic base of pyrrolo[1,2-a]quinolone, were considered. The search for biologically active substances of this series is important and has a practical and theoretical significance.
ChemInform Abstract: Synthesis of Linear Azolo- and Pyridoquinolines from Quinoline Derivatives
ChemInform, 2009
Angular N-tricyclic systems as triazolo [4,5-f]quinolines, triazolo[4,5-h]quinolines, imidazo[4,5-f]quinolines, imidazo[4,5h]quinolines were in the past obtained by connection of either f or h sides of the quinoline ring and both the adjacent carbon atoms of five-membered rings containing nitrogen atoms. Several attempts at obtaining the corresponding linear N-tricycles were made in the last century, but only the angular derivatives were obtained. Since 2000 a new simple pathway, involving suitable quinoline derivatives, which afforded the linear azolo and pyrido quinolines (imidazo[4,5-g]quinolines, triazolo[4,5-g]quinolines and pyrido[2,3g]quinoxalines) has been developed. Several linear N-tricyclic derivatives have shown some interesting pharmaceutical activity.