New Modification of the Intramolecular α-Amidoalkylation for the Synthesis of 2-Acyl-1,2,3,4-tetrahydroisoquinolines

Venkov, Atanas P.; Lukanov, L. K.

doi:10.1055/s-1989-27153

Cited by 35 publications

(10 citation statements)

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“…In another experiment, 2t was also obtained from the oxime 6 in the presence of chloroacetyl chloride and KI in 1,2-dichloroethane at room temperature. 14 These findings also confirmed the formation of oxoiminium ion 15 during these reactions.…”

Section: Methodssupporting

confidence: 62%

A New Application of the Pictet-Spengler Reaction to the Preparation of 4-Substituted 1H-2,3-Benzoxazines

Zheng¹,

Wang²,

Chang³

et al. 2006

Synlett

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Intramolecular coupling reaction of benzylic O-hydroxamates and aldehydes was investigated to afford a variety of 4-substituted 1H-2,3-benzoxazine ring systems in good to excellent yields. The reaction involved an intramolecular C-C bond formation between an N-acyl-or N-sulfonyl-oxoiminium ion with the aryl ring. Under the studied conditions, electron-donating groups in the aryl ring are essential for the desired coupling reactions.

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Section: Methodssupporting

confidence: 62%

A New Application of the Pictet-Spengler Reaction to the Preparation of 4-Substituted 1H-2,3-Benzoxazines

Zheng¹,

Wang²,

Chang³

et al. 2006

Synlett

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“…We then turned our attention to the synthesis of the left segment 7 . Synthesis of 7 commenced with dibromination14 of tetrahydroisoquinoline 20 ,15 which was readily obtained from commercially available homoveratrylamine by a two‐step sequence (Scheme ). After removal of the trifluoroacetyl group, oxidation to dihydroisoquinoline 21 and subsequent treatment with NsCl furnished hemiaminal 22 .…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of (+)‐Yatakemycin

Okano

Tokuyama

Fukuyama

2008

Chemistry An Asian Journal

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A convergent total synthesis of (+)-yatakemycin was accomplished by a 20-step sequence in 13% overall yield. The regioselective ring opening of (S)-epichlorohydrin with a 2,6-dibromophenyllithium derivative enabled us to introduce a chiral carbon center, which was required for the stereoselective construction of the cyclopropane ring. The five aryl-nitrogen bonds in (+)-yatakemycin were constructed by a mild copper-mediated aryl amination that utilized the combination of CuI with CsOAc. The efficient and chemoselective debenzylation of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene was developed. With these new methodologies, the subgram-scale synthesis of (+)-yatakemycin was achieved.

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“…Imines 7b and 10 were also isolated as a mixture with the corresponding aldehyde. (12), 170 (21), 150 (12), 128 (19), 115 (16).…”

Section: Synthesis Of Imines 7a-d and 10mentioning

confidence: 99%

Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones

et al. 2011

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1,2-Disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones are prepared for the first time through an activated Pictet-Spengler reaction of the corresponding imines of 2-(1,4-dimethoxynaphth-2-yl)ethylamine in the presence of an acyl chloride and AlCl(3) followed by an oxidation with silver(II) oxide in nitric acid. Depending on the reaction conditions the N-trichloroacetyl protecting group could be cleaved off, converted to an N-methoxycarbonyl group or transformed to an N-(2-oxoacetamide) moiety. The synthesized 1,2-disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones constitute a new class of quinones, which has not been reported yet.

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New Modification of the Intramolecular α-Amidoalkylation for the Synthesis of 2-Acyl-1,2,3,4-tetrahydroisoquinolines

Cited by 35 publications

References 0 publications

A New Application of the Pictet-Spengler Reaction to the Preparation of 4-Substituted 1H-2,3-Benzoxazines

A New Application of the Pictet-Spengler Reaction to the Preparation of 4-Substituted 1H-2,3-Benzoxazines

Total Synthesis of (+)‐Yatakemycin

Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones

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