Recent approaches to the synthesis of tetrahydrocarbazoles

Abstract

The tetrahydrocarbazole (THC) motif is ubiquitous in natural products and biologically active compounds. THCs can serve as favorable synthetic intermediates or precursors en-route to desired complex natural products. Despite a...

A review on synthesis methods of tricyclic 1,2,3,4-tetrahydrocarbazoles

“…1,2,3,4-Tetrahydrocarbazole [THCz] is a tricyclic aromatic structure consisting of a five membered pyrrole ring fused with one side benzene ring and other side cyclohexane ring respectively [1][2][3]. Tetrahydrocarbazole (THCz) structure is majorly present in natural products and biologically active compounds [4][5][6][7] (Fig. 1).…”

“…A lot of strategy available for the preparation of 1,2,3,4-tetrahydrocarabzole scaffold in literature. However, Fischer indole synthesis approach is most common synthetic method used for the preparation of tetrahydrocarbazole scaffold and also play important role in preparation of various natural products [5,[16][17][18]. Various research groups synthesized tetrahydrocarbazoles based on Fischer indole method using starting material phenyl hydrazine and cyclohexanone using conventional, microwave and catalyst approach.…”

“…In 2020, Ajit Nangare et al and co-workers published the review article on topic synthetic derivatives of aromatic carbazole [19]. TY Chaudhari et al published in detail on topic various synthetic methods to the preparation of tetrahydrocarbazoles [5]. This review will give researchers to idea in short way to find out the preparation of 1,2,3,4-tetrahydrocarbazoles from conventional approach or microwave method or use of catalyst.…”

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

“…Over the past decades, many efficient synthetic methodologies for functionalized carbazole derivatives have been successfully developed [12][13][14][15][16][17][18]. Because indoles are readily available materials, the direct extension of indoles to carbazole skeletons has a great advantage [19][20][21][22][23][24][25][26][27]. Therefore, the Diels-Alder reaction of activated 2-vinylindolines or 3-vinylindolines with diverse dienophiles has become the most attractive strategy for the synthesis of carbazole deriv- atives [28][29][30][31][32][33][34][35][36][37][38][39][40].…”

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels-Alder reaction

“…Over the past decades, many efficient synthetic methodologies for functionalized carbazole derivatives have been successfully developed [12][13][14][15][16][17][18]. Because indoles are much more readily available material, the direct extension of indoles to carbazole skeletons has a great advantage [19][20][21]. Therefore, Diels-Alder reaction of active 2-vinylindolines or 3-vinylindolines with diverse dienophiles has become the most attractive strategy for the synthesis of many carbazole derivatives [22][23][24][25][26][27][28][29][30][31][32][33][34].…”