Synthesis of substituted 1-styryl-3,4-dihydroisoquinolines

Harmon, Robert E.; Jensen, Bruce L.; Gupta, Surendra K.; Nelson, J. D.

doi:10.1021/jo00828a066

Cited by 14 publications

(7 citation statements)

References 4 publications

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“…The Skoda group has recently reported on the mechanism of inhibition of E. coli growth by la, and detailed conditions of the hydrolytic fission of the oxazinedione ring. 7 Our interest in the regioselective synthesis of alkyl-and halooxazinediones as agents against neoplastic and proto-zoan disease, particularly malaria, leads us to detail improved synthetic pathways to these heterocycles.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of ring-fused pyrroles. II. 1,3-Dipolar cycloaddition reactions of muchnone derivatives obtained from tetrahydroisoquinoline-1-carboxylic acids

Hershenson¹

1975

J. Org. Chem.

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The reactions of mesoionic oxazolium 5-oxides (munchnones) derived from 1,2,3,4-tetrahydroisoquinoline-lcarboxylic acids (la, lb, and 5) are reported and involve the 1,3-dipolar cycloaddition to the acetylenic dipolarophiles, dimethyl acetylenedicarboxylate and phenylacetylene. In the latter case, the reaction was found to be regiospecific, yielding 7a and 7b, respectively, as the only products. An isomeric pvrrolo[2,l-n|isoquinoline (8) was prepared by an unambiguous route and a comparison of the PMR spectra of 7a and 8 is presented. Furthermore, irradiation of a methanolic solution of 7a in the presence of trace amounts of iodine resulted in a photocylization yielding the indolizinophenanthrene (9a). Unsuccessful attempts at the preparation of the analog, 9b, via photocyclization or Pschorr cyclization reactions are also discussed.

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Section: Methodsmentioning

confidence: 99%

Synthesis of ring-fused pyrroles. II. 1,3-Dipolar cycloaddition reactions of muchnone derivatives obtained from tetrahydroisoquinoline-1-carboxylic acids

Hershenson¹

1975

J. Org. Chem.

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“…The JV-Methyltetrahydroisoquinolines, 6. Sodium borohydride (2.8 g, 0.075 mol) was added in small portions to a stirred solution of 6.5 g (0.01 mol) of 5a in 500 ml of MeOH.…”

Section: Experimental Section29mentioning

confidence: 99%

“…Evaporation of the solvent gave a residue which was decomposed with water and partitioned between water and benzene. The benzene was washed (H2O), dried (K2CO3), and evaporated to a colorless syrup which crystallized from ether-hexane to give 4.5 g (86%) of 6a, mp 92-93°: NMR (CDC13) 7.22 (d, J = 9 Hz, 2, aromatic), 6.92 (d, J = 9 Hz, 2, aromatic), 6.62 (broad s, 2, aromatic), 6.47 (d, J = 15 Hz, 1, Ha), 5.83 (two d's, J = 15 and 8.5 Hz, 1, Ht,) 5.09, 5.01 (each s, each 2 H, OCH2CeH5), 3.85 (s, 3, OCH3), 2.42 (s, 3, NCH3).…”

Section: Experimental Section29mentioning

confidence: 99%

“…The solvent was evaporated, and the residual sodium salt was dissolved in water, washed (CHCI3), acidified (HC1), and extracted (CHClg). The CHCI3 extract was dried (MgS04) and evaporated to yield 1.6 g (62%) of crystalline 15: mp 86-88°from EtOH; NMR (CDCI3) 7.30 (m, 5, aromatic), 6.60 (m, 5, aromatic), 3.78 (s, 6, 2 OCH3), 2.95 (m, 4, C-3 and C-4).…”

Section: Experimental Section29mentioning

confidence: 99%

“…The compounds oxidized were 7 and 8, which were prepared (Scheme I) by the method generalized by Harmon and his coworkers. 6 The actual reactions used, however, are substantially different from those previously recorded7-9 in that the side chain double bond is left in place until the final debenzylation step (6 to 7 and 8). Using this sequence, the intermediates were easier to crystallize and work with.…”

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confidence: 91%

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