An approach to functionalized carbazoles from Z-enoate propargylic alcohols. A unified total synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4
Тип публикации: Journal Article
Дата публикации: 2022-08-17
scimago Q1
wos Q2
white level БС1
SJR: 1.037
CiteScore: 7.4
Impact factor: 4.2
ISSN: 13597345, 1364548X
PubMed ID:
36000534
Materials Chemistry
Metals and Alloys
Surfaces, Coatings and Films
General Chemistry
Ceramics and Composites
Electronic, Optical and Magnetic Materials
Catalysis
Краткое описание
Development of an acid catalyzed, intramolecular benzannulation of indoles for the synthesis of functionalized carbazoles has been reported. The indole appended Z-enoate propargylic alcohols have been employed. The N-EDG-indoles involve the 5-exo-dig cyclization followed by 1,2-migration to give the carbazole-butenoates, whereas the N-EWG-indoles undergo the Z-enoate assisted Meyer-Schuster rearrangement to give the dihydrocarbazole-4-oxo-butanoates. Utilizing one of the 2-methyl-carbazole-butyraldehyde (obtained from the corresponding carbazole-butanoate) as the key intermediate, we have developed a simple approach for an efficient synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4.
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Roy D., Tharra P., Baire B. An approach to functionalized carbazoles from Z-enoate propargylic alcohols. A unified total synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4 // Chemical Communications. 2022. Vol. 58. No. 73. pp. 10210-10213.
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Roy D., Tharra P., Baire B. An approach to functionalized carbazoles from Z-enoate propargylic alcohols. A unified total synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4 // Chemical Communications. 2022. Vol. 58. No. 73. pp. 10210-10213.
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TY - JOUR
DO - 10.1039/d2cc03526j
UR - https://xlink.rsc.org/?DOI=D2CC03526J
TI - An approach to functionalized carbazoles from Z-enoate propargylic alcohols. A unified total synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4
T2 - Chemical Communications
AU - Roy, Debayan
AU - Tharra, Prabhakararao
AU - Baire, Beeraiah
PY - 2022
DA - 2022/08/17
PB - Royal Society of Chemistry (RSC)
SP - 10210-10213
IS - 73
VL - 58
PMID - 36000534
SN - 1359-7345
SN - 1364-548X
ER -
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@article{2022_Roy,
author = {Debayan Roy and Prabhakararao Tharra and Beeraiah Baire},
title = {An approach to functionalized carbazoles from Z-enoate propargylic alcohols. A unified total synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4},
journal = {Chemical Communications},
year = {2022},
volume = {58},
publisher = {Royal Society of Chemistry (RSC)},
month = {aug},
url = {https://xlink.rsc.org/?DOI=D2CC03526J},
number = {73},
pages = {10210--10213},
doi = {10.1039/d2cc03526j}
}
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Roy, Debayan, et al. “An approach to functionalized carbazoles from Z-enoate propargylic alcohols. A unified total synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4.” Chemical Communications, vol. 58, no. 73, Aug. 2022, pp. 10210-10213. https://xlink.rsc.org/?DOI=D2CC03526J.
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