Pyrrolo isoquinoline derivatives

Oxidations of several l-(3,4-dimethoxyphenyl)-2-(heteroaryl)ethanes with BTIB/Et20 BF3 have also been investigated (01SL1161). The 2-thienyl and 7V-pyrrolyl analogs 114 and 115 gave the naphthothiophene and pyrrolo-isoquinoline derivatives 116 (52%) and 117 (48%), respectively. However, the 2-furyl, 7V-methyl-2-pyrrolyl, and 6-methoxy-2-pyridyl congeners failed to give phenanthroid heterocycles under these conditions. 

Study of this receptor model led to the design of a series of 4a,8a-trans-pyrrolo [2,3-g] isoquinoline derivatives (e.g., Ro 22-1319, la)... 

Treatment of N-2,4-dinitrophenylpyridinium chloride (778) with phenyl-hydrazine in acetic acid causes reductive cyclization to yield the pyrido[l,2-ajimidazole (779). 3-Aminocrotononitrile, MeC(NH2)=CHCN, condenses with quinoline 1-oxide and isoquinoline 2-oxide to form the tricyclic compounds (780) and (781), respectively." The imidazo[5,l-a]isoquinoline derivative (783) is obtained by the action of phenyl isothiocyanate on the sodium salt of the Reissert compound (782)." ° Triethyl phosphite reduces the o-nitrophenyldipyr-rolylmethane (784 R=N02) to the nitrene (784 R = N), which forms the pyrrolo[3,2-6]quinoline derivative (785) by an intramolecular insertion reac-tion." 3-Amino-177-isoindole (786) reacts with acetylacetone in the presence of perchloric acid to yield the pyrimidoisoindolium salt (787). ... 

Peng W, Zhu S (2001) Reactions of N-benzyl-pyridinium or -isoquinolinium yhdes with ethyl 3-fluoro-3-(fluoroalkyl)acrylates to give fluoroalkylsubstituted indolizine and pyrrolo[2,l-a] isoquinoline derivatives. J Chem Soc Perkin Trans 1 23 3204-3210... 

Benzoylketene 372 undergoes a [3+2] cycloaddition reaction to the isoquinolinium ylide 373 to afford pyrrolo[2.1-a]-isoquinoline derivative 374. ... 

Pyrrolo[2,l-a]isoquinoline derivatives (27) were synthesized using Cgo-Bodipy dyads (28) as excellent photosensitizers (Scheme 13)/ Direct irradiation of glycine methyl ester to Ceo afforded [3 - - 2] cycloadduct/ Akasaka and his coworkers found the photocycloaddition of 2-ada-mantane-2,3-[3ff]diazirine and disilyliranes to Cso-metallofullerenes/ Intra- and inter-molecular photocycloaddition of alkenes to coumarin, quinolone, and isoquinolone derivatives have been reported by several groups. Griesbeck et al. found that the intramolecular photocycloaddition of cyclohexene moiety to coumarin (29) was catalysed by molecular ojygen. [2 + 2] Photocross dimer (33) of coumarin derivative (31) and 5-fluorouracil derivative (32) was obtained by laser irradiation/ Bach reported enantioselective intramolecular photocycloaddition of coumarins (34) to alkenes catalysed by a chiral Lewis acid (36) (Scheme 14)/ ... 

S. Monsal, A. Maity, R. Paira, M. Banerjee, YP. Bharitkar, A. Hazra, S. Banerjee, N.B. Mondals, Efficient synthesis of novel tetrahydropyr-rolo[3, 4 3.4]pyrrolo[2.1-fl] isoquinoline derivatives via simple and convenient MCR in aqueous micellar system. Tetrahedron Lett. 53 (2012) 1288-1291. 

A new synthetic approach to pyrrolo[2,l-a]isoquinolines, important moieties found in natural products (e.g., lamellarins), has been reported <07S1003>. /V-Alkylation of Bischler-Napieralski derived isoquinolines with ethyl bromoacetate gave the corresponding quaternary... 

The importance of azaellipticines is illustrated by the fact that 204 (BD-40) is undergoing clinical trials 10,98). Using their new 1-chloroellipticine synthesis (Scheme 20), Bisagni et al. 74) have described an extremely concise route to 10-chloro-5,6-dimethyl-5ff-pyrido[3, 4 4,5]pyrrolo[2,3-g]isoquinoline (208) and the side-chain amine derivatives 209-211 (Scheme 35). Formylation of 1-methyl -5-azaindole (205), followed by reaction with the lithiochloropyridine 124, gave... 

This methodology with some variations has been utilized in the synthesis of numerous heterocyclic systems, such as heterocycle-fused quinolinone derivatives [391], l,4-benzodiazepin-2-ones [392], benzo-, naphtho- and heterocycle-fused pyrrolo[2,l-c][l,4]diazepines [393], quinolinone or pyrrolidinone derivatives [394], dibenzo[fl,c]phenanthridines [395], thiazolo-fused quinolinones [396], isoindolinone and isoquinolin-2-one derivatives [397], indoline derivatives [398], 5-aroyl-pyrrolidinones [399,400], indazolone derivatives [401,402], substituted indolizidinones [403], 1-arylpyrrolopyrazinones [404], stmcturally diverse... 

SCHEME 18 One-pot three-component reaction of variously substituted isoquinolines, 2-bromoacetophenone, and N-arylmaleimide derivatives to form tetrahydropyrrolo-[3, 4 3.4]pyrrolo[2.1-fl]isoquinoline-9,ll-diones. 

Monsal and coworkers have achieved the construction of pyrrolidine nucleus in the synthesis of tetrahy-dropyrrolo[3, 4 3.4]pyrrolo[2.1-fl]isoquinoline-9,ll-diones 57 derivatives in an aqueous micellar medium [53]. The S5mthesis involves a one-pot three-component reaction of variously substituted isoquinolines 54, 2-bromoacetophenone 55, and N-arylmaleimide derivatives 56 in the presence of triethylamine as a base (Scheme 18). The preliminary investigation indicated that the presence of surfactant was essential for the success of reaction. Accordingly, the reactions were carried out in cationic, anionic, and nonionic surfactants well above their critical micelle concentrations (CMC). The maximum yields were obtained in cetyltrimethylammonium bromide (CTAB) (CTABiCMC value 0.29 mM at 80mM concentration). The mechanism of formation involves an in situ generation of isoquinolinium ylides followed by [2 -h3] cycloaddition of N-aryl maleimides. 

Lamellarins belong to a new dass of hexacyclic alkaloids including a pyrrole and an isoqtunoline the nitrogen atom is common to the two rings. Lamellarins are derived from pyrrolo[2-l,a]isoquinoline or pyrrolo[2-l,a]dihydroisoqui-noline according to the degree of unsaturation of the 5-6 bond. 

The BINOL derivative (119) has been also successfully used as a chiral catalyst in synthesis of oc-brominated enecarbamates (131), indene derivatives possessing a stereogenic spirocyclic carbon center (132), spiroketals (133), hexahydropyrrolo[3,2-c]quinolines (134), pyrrolo[2,l-a]isoquinolines (135), and adducts of the Robinson-type reaction (136). °... 

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