5257-08-9Relevant academic research and scientific papers
A one-pot "back-to-front" approach for the synthesis of benzene ring substituted indoles using allylboronic acids
Karan, Ganesh,Sahu, Samrat,Maji, Modhu Sudan
, p. 5274 - 5277 (2021/06/06)
Synthesis of only benzene ring functionalized indoles and poly-substituted carbazoles is reported via a one-pot triple cascade benzannulation protocol. Usage of differently substituted and readily accessible allylboronic acids as a 3-carbon annulating partner enables diverse aliphatic and aromatic substitution patterns, which is still a daunting task. This scalable synthetic protocol tolerates broad scope, thus enabling further downstream modifications. As an application, carbazole based natural products glycozoline and glycozolinol were synthesized. This journal is
Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates
Mandal, Tirtha,Chakraborti, Gargi,Karmakar, Shilpi,Dash, Jyotirmayee
, p. 4759 - 4763 (2018/08/24)
The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.
Transition metals in organic synthesis - Part 83#: Synthesis and pharmacological potential of carbazoles
Choi, Taylor A.,Czerwonka, Regina,Forke, Ronny,Jaeger, Anne,Knoell, Jan,Krahl, Micha P.,Krause, Tilo,Reddy, Kethiri R.,Franzblau, Scott G.,Knoelker, Hans-Joachim
, p. 374 - 385 (2008/12/23)
A series of carbazole derivatives with promising pharmacological properties has been prepared using either an iron-mediated or a palladium-catalyzed synthetic approach. The carbazole alkaloids carbazoquinocin C, carbazomadurin A and B, epocarbazolin A and
Transition metals in organic synthesis, part 82.1 First total synthesis of methyl 6-methoxycarbazole-3-carboxylate, glycomaurrol, the anti-TB active micromeline, and the furo[2,3-c]carbazole alkaloid eustifoline-D
Forke, Ronny,Krahl, Micha P.,Krause, Tilo,Schlechtingen, Georg,Kn?lker, Hans-Joachim
, p. 268 - 272 (2007/10/03)
The palladium(0)-catalyzed animation followed by palladium(II)-catalyzed oxidative cyclization of the resulting diarylamine provides a short route to a series of 6-oxygenated carbazole alkaloids: glycozoline, 3-formyl-6- methoxycarbazole, methyl 6-methoxy
A REGIOSPECIFIC SYNTHESIS OF CARBAZOLES VIA CONSECUTIVE PALLADIUM-CATALYZED CROSS-COUPLING AND ARYNE-MEDIATED CYCLIZATION
Iwao, Masatomo,Takehara, Hirokazu,Furukawa, Sunao,Watanabe, Mitsuaki
, p. 1483 - 1488 (2007/10/02)
A regiospecific synthesis of carbazoles has been developed using palladium-catalyzed cross-coupling of N-(tert-butoxycarbonyl)-2-tributylstannylanilines with 2- or 3-bromochlorobenzene followed by aryne-mediated cyclization as the key reactions.The carbazole alkaloids, glycozolinine and glycozolidine, were synthesized using this procedure.
Structure and Synthesis of Glycozolinol, a New Carbazole Alkaloid from Glycosmis pentaphylla (Retz) DC.
Bhattacharyya, P.,Sarkar, T.,Chakraborty, A.,Chowdhury, B. K.
, p. 49 - 51 (2007/10/02)
Glycozolinol, a new carbazole alkaloid isolated from Glycosmis pentaphylla (Retz) DC. has been formulated as 6-hydroxy-3-methylcarbazole (I) based on physical data, chemical reactions and spectral evidences.The structure (I) has been confirmed by synthesis.
