3,6-Bis(5’-bromo-3’-indolyl)-1,4-dimethypiperazine-2,5-dione

Crooke, Stephen N.; Davis-McGibony, Michele; Whitlock, Christine R.

doi:10.3390/m627

Cited by 1 publication

(2 citation statements)

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“…Displacement of these labile bromides readily occurs with a range of nucleophiles SR, OR, NR 2 , alkyl, and aryl . In situ methanolysis of 166 afforded 169 (R = OMe), which was used in the synthesis of asymmetric 2,5-diketopiperazines .…”

Section: Reactionsmentioning

confidence: 99%

See 1 more Smart Citation

2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products

Borthwick¹

2012

Chem. Rev.

755

726

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amide with a bivalent electrophile. For example, the aminoamide adducts 118 of tryptamine and an L-amino acid were reacted with a range of pyruvic acids to give the ketoamides 119. These were cyclized with HCl in EtOAc to give the 2,5-DKP ring that underwent a Pictet−Spengler-type condensation to give the tetrahydro-β-carboline and tetrahydroisoquinoline 2,5-diketopiperazines 120a and 120b. 102 However, reacting 118 (R = 5,6-DiMeO, R 1 = Me) with pyruvic acid gave the hydroxylactam 121 as a mixture of diastereroisomers rather than the ketoamide, and they underwent cyclization in the presence of HCl to give the corresponding tetrahydroisoquinoline 2,5-diketopiperazine derivatives 120b (Scheme 30). The L-amino acids were promoters of 1,4-chirality transfer with up to 100% diastereomeric excess (de). The stereochemistry of the final 2,5-diketopiperazines strongly depended on the structure of the L-amino acids used: acyclic amino acids gave predominantly the (R)-configuration at the newly created stereogenic center, whereas L-proline afforded the opposite configuration 122.

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Section: Reactionsmentioning

confidence: 99%

“…In situ methanolysis of 166 afforded 169 (R = OMe), which was used in the synthesis of asymmetric 2,5-diketopiperazines . The dibromide 167 (R 1 = R 2 = Me) has been used in the synthesis of the natural product dragmacidin B 171 by reaction with 6-bromoindole to give 170 followed by reduction …”

Section: Reactionsmentioning

confidence: 99%