Pyrrolo quinoline synthesis

E rrolo[3,2-i]quinolines synthesis, 4, 260, 517 Pyrrolo[3,2-c]quinolines synthesis, 4, 527 Pyrrolo[3,4-6]quinolines synthesis, 4, 517... 

Scheme 15.118 Pyrrolo[l,2-Q ]quinoline synthesis via a Au-catalyzed tandem hydroamina-tion/alkyne addition/hydroarylation.

Other indoles that have been prepared using the Sonogashira coupling and cyclization sequence include 5,7-difluoroindole and 5,6,7-trifluoroindole [219], 4-, 5-, and 7-methoxyindoles and 5-, 6-, and 7-(triisopropylsilyl)oxyindoles [220], the 5,6-dichloroindole SB 242784, a compound in development for the treatment of osteoporosis [221], 5-azaindoles [222], 7-azaindoles [160], 2,2-biindolyls [223,176], 2-octylindole for use in a synthesis of carazostatin [224], chiral indole precursors for syntheses of carbazoquinocins A and D [225], a series of 5,7-disubstituted indoles [226], a pyrrolo[2,3-eJindole [226], an indolo[7,6-g]indole [227], pyrrolo[3,2,l-y]quinolines from 4-arylamino-8-iodoquinolines [228], optically active indol-2-ylarylcarbinols [229], 2-alkynylindoles [176], 7-substituted indoles via the lithiation of the intermediate 2-alkynylaniline derivative [230], and a variety of 2,5,6-trisubstituted indoles [231], This latter study employs tetrabutylammonium fluoride, instead of Cul or alkoxide, to effect the final cyclization of 215 to indoles 216 as summarized here. 

Vilsmeier reaction, 4, 1051 Furo[3,2-6]pyrroles MO calculations, 6, 979 synthesis, 4, 1069 6, 1009 Furo[3,4-a]pyrrolo[2,1,5-cd]indolizine nomenclature, 1, 22 Furopyrylium salts, 4, 993-995 Furoquinolines biosynthesis, 4, 992 occurrence, 4, 988 pharmacology, 4, 992 reactions, 4, 988 synthesis, 4, 989 Furo[3,2-c]quinolines, 4, 991 Furo[3,4-fe]quinoxaline, 1,3-diphenyl-synthesis, 4, 993 Furoquinoxalines, 4, 992 Furo[2,3-6]quinoxalines synthesis, 4, 992 Furosemide toxicity, 1, 136 Furospinulosin UV spectra, 4, 587 Furospongin-I mass spectrometry, 4, 583 Furo[3,4-d][l,2,3]triazole, 2,6-dihydro-synthesis, 6, 996 Furo[3,4 -d][ 1,2,3]triazoles synthesis, 6, 996 Furoxan, 4-amino-3-aryl-tautomerism, 6, 404 Furoxan, 4-amino-3-methyl-synthesis, 4, 414 Furoxan, 4-aryl-3-methyl-rearrangement, 6, 408 Furoxan, 3-aryl-4-nitro-synthesis, 6, 414 Furoxan, 4-benzoyl-3-methyl-oxime... 

B. Das et al. have also elaborated the microwave-assisted synthesis of Mappicine ketone, a potent antiviral lead compound derived from the natural product Camptothecin. The naturally occurring pyrrolo [ 3,4-6 ] quinoline... 

Fischer indole cyclization and transformation of a nitrile to an ester (Pinner synthesis) to yield diethyl 5-hydroxy-1 T/-pyrrolo[2,3-/]quinoline-2,7-dicarboxylate (183) was performed in one step by... 

During their early investigations of harmine, Perkin and Robinson attempted a synthesis of what they thought to be isoharman. The 2-quinolone amide (74) was cyclized with phosphoryl chloride to a chloro compound (75), which gave 2.ff-pyrrolo[2,3-6]quinoline (76, R = H) with tin and hydrochloric acid, and its 3-methyl derivative (75, R = Me) with methylmagnesium iodide. The name quinindole ... 

Pyrido[2,3-h]indoles (a-carbolines), synthesis and reactivity of 84KGS435. Pyrido[2,3-c]indoles (/S-carbolines), biochemistry of 83MIIO. Pyrido[3,2-c]indoles, tetrahydro- (tetrahydro-y-carbolines) 73KGS291. 3//-Pyrrolo[2,3-c]quinolines 78H(9) 1617. 

The Com synthesis was applied for the synthesis of pyrrolo[3,2- if]- and pyrrolo[2,3-0]quinolines (equation 120). Even during the synthesis of an enaminone from a... 

More recently, Lautens has also employed l-(2-iodophenyl)-pyrrole as a bifunctional aryl iodide/acceptor for the synthesis of substituted pyrrolo[l,2]quinolines (Scheme 34)[82], During Catellani s application of the Cassar-Sonogashira reaction to the ort/m-alkylation sequence [70] it was found that alkynes can undergo further carbopalladation reactions with arylpalladium(II) species. It was this reactivity which led Lautens to explore the use of bromoalkylalkynes as species which can undergo an ort/zo-alkylation, followed by a cyclocarbopalladation onto the alkyne,... 

Synthetic approaches to the construction of pyrrolo[3,2-c]quinoline systems were compiled in a review by Nyerges <04H1685>. Recent advances in the synthesis of the Martinelline alkaloids are also described. 

The versatility of this methodology is illustrated by Husson s regiocontrolled synthesis of pyrrolo[3,4-b]quinolin-9-ones (path A) and pyrrolo[2,3-c]quinolin-4-ones (path B) from l,2,4,5-tetrahydro-y9-carbolines 13a and 13b (Scheme 32) [65]. 

Similar methodology was employed for the synthesis of methyl-1, 3-dihydro-2H-pyrrolo[3,4- ]quinoline-2-carboxylate 162 in 65% yield and methyl-l,2-dihydro-3H-pyrrolo[3,4-h]quinoline-3-carboxylate 163 in 25% yield from commercial starting materials 160 and 161 (Scheme 31) (07S3319). 

A versatile synthesis of pyrrolo-annelated quinolines has been reported to occur via alkylation of the VNS products, orf/to-nitroaryl-substituted acetonitriles, with a-bromoketones. The obtained ketonitriles can be reduced under mild conditions with tin(ll) chloride in ethyl acetate-ethanol mixture into quinoline-4-carbonitriles [214]. The same reaction sequence has been applied to 5-nitroindol-4-yl- and 4-nitroindol-5-yl-acetonitriles to obtain tricyclic 4-cyano-2-phenyl derivatives of pyrrolo[3,2-/ - and pyrrolo[2,3-/i]-quinolines (Scheme 91) [214]. 

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