62698-34-4Relevant academic research and scientific papers
Br?nsted Acid Promoted Thermal-Ring-Rearrangement of Fluorenopyrans to 2-(1H-Inden-3-yl)-9H-fluoren-3-ols Bearing Two All-Carbon-Quaternary Centres
Jose, K. V. Jovan,Khan, Tabassum,Praveen, Dudam,Rajesh, P.,Yaragorla, Srinivasarao
, (2020)
4-Aryl-fluorenopyrans bearing quaternary centre at C2 and C6 positions underwent a thermal-ring-rearrangement with a catalytic amount of pTsOH to furnish 2-(1H-inden-3-yl)-9H-fluoren-3-ols with two all carbon-quaternary centres, in which one is retained a
Gold-catalyzed tandem annulations of pyridylhomopropargylic alcohols with propargyl alcohols
Li, Xue-Song,Xu, Dan-Tong,Niu, Zhi-Jie,Li, Ming,Shi, Wei-Yu,Wang, Cui-Tian,Wei, Wan-Xu,Liang, Yong-Min
supporting information, p. 832 - 836 (2021/02/16)
A gold-catalyzed tandem annulation of propargylic alcohols and pyridylhomopropargylic alcohols is achieved, providing an atom-economical approach to a diverse set of polycyclic dihydrobenzofurans in good yields. The reaction proceeds via the 5-endo-dig cyclization/Meyer?Schuster rearrangement/Friedel?Crafts-type pathway. In this way, three C?C bonds and one C? O bond form to give a polycyclic skeleton in a one-pot process. Moreover, the products exhibit unique optical properties, which reveal their potential application value.
Calcium-Catalyzed Intramolecular Hydroamination-Deacylation Reaction of in situ formed β-Amino Allenes
Yaragorla, Srinivasarao,Latha, Dandugula Sneha,Rajesh, Pallava
supporting information, p. 5486 - 5492 (2021/12/10)
We have developed a simple, One-Pot, three-component reaction of tert-propargyl alcohols, primary amines and acyl ketones to synthesize fully substituted pyrroles and pyridine derivatives in good to excellent yields with large substrate diversity. An eco-friendly calcium catalyst catalyzes the reaction to form the key intermediate β-amino allene that undergoes subsequent Thorpe-Ingold effect assisted hydroamination and aromaticity driven deacylation reaction to yield fully substituted five and six-membered azacyclic compounds. (Figure presented.).
Synthesis of 1H-Pyrrolo[1,2-a]indoles via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with 2-Ethynylanilines
Du, Li-Juan,Han, Ya-Ping,Liang, Yong-Min,Zhang, Hong-Yu,Zhang, Yuecheng,Zhao, Jiquan
supporting information, (2020/03/04)
A novel highly efficient, environmentally benign Lewis acid-catalyzed, and protection-free protocol for the construction of valuable polycyclic products bearing a 1H-pyrrolo[1,2-a]indole scaffold is described, starting from readily available propargylic alcohols and 2-ethynylanilines. The one-pot transformation entails the cleavage of one C?O bond, and the construction of two C?N bonds and one C?C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.
In Situ Generation of Allenes and their Application to One-Pot Assembly of Functionalized Fluoreno[3,2-b]furans by Calcium-Catalyzed, Regioselective, 3-Component Reactions
Rajesh, Pallava,Yaragorla, Srinivasarao
supporting information, p. 7243 - 7251 (2020/12/01)
We have developed a novel synthetic methodology for the preparation of tetra-annulated fluorenofurans and fluorenopyrans using calcium(II)-catalyzed one-pot, three-component reaction. In this reaction, tert-propargyl alcohols react with 1,3-dicarbonyls to form tetra-substituted allenes, which are subsequently undergoing regiodivergent annulation with sec-propargyl alcohols to produce the fluorene-fused furan compounds. Broad substrate scope, regioselectivity, gram-scale synthesis, and benzylic functionalization of products are some of the highlights of this protocol.
Regiospecific formal [3 + 2] annulation of: Tert -propargyl alcohols with acyclic 1,3-diketones via the cycloisomerization of homoallenyl ketones
Yaragorla, Srinivasarao,Rajesh
supporting information, p. 1924 - 1928 (2019/02/20)
A one-pot, regiospecific synthesis of dihydrofurans bearing a quaternary centre and tetrasubstituted furans is developed from the formal [3 + 2] annulation of tert-propargyl alcohols and 1,3-diketones under Ca(ii)/DBU conditions. The reaction proceeds through the SN2I mechanism to form homoallenyl ketone and a subsequent cycloisomerization to yield novel and new chemical entities of privileged scaffolds.
An efficient Benzannulation protocol for the synthesis of 9,9-Diphenyl-9H-fluorenols using Intramolecular Allene Friedel–Crafts Annulation
Yaragorla, Srinivasarao,Rajesh
supporting information, p. 5740 - 5748 (2019/08/20)
Herein we report a one-pot cascade benzannulation protocol for the synthesis 9,9-diaryl-9H-fluorenol, a key structure of many important natural products which exhibit the significant biological activities particularly phosphodiesterase-4 (PDE4) inhibitory activity. This approach proceeds through the annulation of tert-propargyl alcohols with 2-methyl acetylacetone through an intramolecular allene Friedel–Crafts reaction using Ca(OTf)2 as the environmentally benign catalyst. Synthetic transformations of these compounds to useful materials are also presented here with the aid of cross-coupling and RCM reactions.
Lewis Acid-Catalyzed Formal [3+3] Annulation of Propargylic Alcohols with 4-Hydroxy-2H-chromen-2-ones
Han, Ya-Ping,Li, Xue-Song,Li, Ming,Zhu, Xin-Yu,Liang, Yong-Min
supporting information, p. 2796 - 2800 (2018/08/17)
A Lewis acid-catalyzed formal [3+3] cascade annulation strategy for the formation of diverse tricyclic compounds possessing functionalized pyrano[3,2-c]chromen-5(2H)-one fragments has been developed using propargylic alcohols and 4-hydroxy-2H-chromen-2-on
Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with (Z)-2-Styryl-1H-Indoles
Li, Xue-Song,Han, Ya-Ping,Zhu, Xin-Yu,Xia, Yu,Wei, Wan-Xu,Li, Ming,Liang, Yong-Min
supporting information, p. 4441 - 4445 (2018/10/15)
A novel copper(II) trifluoromethanesulfonate-catalyzed intermolecular cascade annulation strategy for the construction of a great variety of pentacyclic compounds possessing valuable carbazole fragments was developed employing propargylic alcohols and (Z)-2-styryl-1H-indoles as the initial substrates. This protocol, which entails a sequential Meyer-Schuster rearrangement/isomerization/-cyclization cascade, enables facile and atom-economical access to various pentacyclic compounds with broad functional-group tolerance in good yields under mild conditions. The conversion could be efficiently scaled up to gram quantities, accentuating a potential application of this work. (Figure presented.).
Ca(II)-Mediated Regioselective One-pot Sequential Annulation of Acyclic compounds to Polycyclic Fluorenopyrans
Yaragorla, Srinivasarao,Rajesh,Pareek, Abhishek,Kumar, Ankit
supporting information, p. 4422 - 4428 (2018/10/20)
Herein we report a facile synthesis of tetracyclic fluorenopyrans from simple acyclic reactants, propargyl alcohols and 3-methylpentane-2,4-dione under calcium catalysis. This one-pot, 3-component reaction proceeds through a sequential allene formation, F
