53778-26-0Relevant academic research and scientific papers
Regioselective competitive synthesis of 3,5-bis(het) aryl pyrrole-2-carboxylates/carbonitriles vs. β-enaminones from β-thioxoketones
Sharath Kumar, Kothanahally S.,Ananda, Hanumappa,Rangappa, Shobith,Raghavan, Sathees C.,Rangappa, Kanchugarakoppal S.
supporting information, (2021/09/28)
An easily adaptable protocol for the synthesis of 3,5-bis(het)aryl-2-carboxylate/nitrile pyrroles and the related 2,3,5-tri(het)aryl-pyrroles with complementary regioselectivity from the corresponding 1,3-bis(het)aryl-1,3-monothio diketones or β-enaminone precursors has been reported. Initially, regioselective base catalyzed condensation of glycine ethyl/methyl esters or aminoacetonitrile with 1,3-bis(het)aryl-1,3-monothio diketones give β-enaminones, which then in-situ undergoes cyclization to form 3,5-bis(het)aryl-2-carboxylate/nitrile pyrroles. The synthesis of 2,3,5 tri substituted pyrroles with full control over 3rd & 5th position on pyrrole ring is the noteworthy feature of this protocol. Although the product yields are moderate to good, the method offers a facile regioselective entry to 2,3,5 trisubstituted pyrroles without the aid of transition metal.
DBU-promoted tandem Michael-addition/cyclization for the synthesis of polysubstituted pyrroles
Yang, Tianyu,Wang, Ke-Hu,Huang, Danfeng,Li, Pengfei,Deng, Zhoubin,Su, Yinpeng,Hu, Yulai
, p. 2291 - 2297 (2019/03/06)
An efficient and transition-metal-free method for the synthesis of the structurally diversified pyrroles is described. Various α,β-unsaturated ynones reacted with N-substituted ethyl glycine ethyl ester hydrochlorides in the presence of DBU to form the co
2,3,5 TRISUBSTITUTED PYRROLE DERIVATIVES AS TOPOISOMERASE INHIBITORS AND THERAPEUTIC USES THEREOF
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, (2017/03/14)
The compounds of Formula (1) having topoisomerase inhibitory effect includes [Formula should be inserted here] wherein, R1 is selected from a group consisting of H, OR5, optionally substituted C1-C12 alkyl, haloalkyl, C2-C12alkenyl, C2-C12alkynyl, C1-C12alkyloxy, C1-C12haloalkyloxy, C2-C10 heteroalkyl, C3- C12 cycloalkyl, C3-C12cycloalkenyl, C2- C12heterocycloalkyl, C2-C2 heterocycloalkenyl, C6-C18aryl, and C1-C18heteroaryl; R2, R3 and R4 are independently selected from a group consisting of H, halogen, CN, - NO2, SH, CF3, OH, CO2H, CONH2, OCF3, optionally substituted C1-C12alkyl, optionally substituted C1-C12haloalkyl optionally substituted C2-C12alkenyl, optionally substituted C2- C12alkynyl, optionally substituted C1-C12alkyloxy, optionally substituted C1- C12haloalkyloxy, optionally substituted C2-C12heteroalkyl, optionally substituted C3- C12cycloalkyl, optionally substituted C3-C12 cycloalkenyl, optionally substituted C2-C12 heterocycloalkyl, optionally substituted C2-C12 heterocycloalkenyl, optionally substituted C6- C18aryl, and optionally substituted C1-C18heteroaryl; R5 is selected H, optionally substituted C1-C12alkyl, optionally substituted C2- C12alkenyl, optionally substituted optionally substituted C1-C12 haloalkyl, optionally substituted C3-C12cycloalkyl, optionally substituted C6- C18aryl, and optionally substituted C1- Ci18heteroaryl; or a pharmaceutically acceptable salt, N-oxide, or prodrug thereof.
Transition Metal-Free Synthesis of 3-Alkynylpyrrole-2-carboxylates via Michael Addition/Intramolecular Cyclodehydration
Teng, Qing-Hu,Xu, Yan-Li,Liang, Ying,Wang, Heng-Shan,Wang, Ying-Chun,Pan, Ying-Ming
supporting information, p. 1897 - 1902 (2016/07/06)
A transition metal-free and efficient method for the synthesis of 3-alkynylpyrrole-2-carboxylates from diynones and glycine esters or 2-aminoacetophenone hydrochloride has been developed. This transformation provides a large range of substituted pyrroles in good to excellent yields with the elimination of water as the only by-product. The detailed mechanistic studies elucidated that this transformation involves a Michael addition/intramolecular cyclodehydration process. (Figure presented.) .
Copper-promoted oxidative coupling of enamides and alkynes for the synthesis of substituted pyrroles
Zhao, Mi-Na,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 1839 - 1842 (2014/03/21)
An efficient copper-promoted oxidative coupling of enamides with alkynes has been developed for the synthesis of substituted pyrroles. The reaction proceeded through C-H and N-H bond functionalization of enamides under mild conditions.
One-pot synthesis of pyrrole-2-carboxylates and -carboxamides via an electrocyclization/oxidation sequence
Imbri, Dennis,Netz, Natalie,Kucukdisli, Murat,Kammer, Lisa Marie,Jung, Philipp,Kretzschmann, Annika,Opatz, Till
, p. 11750 - 11758 (2015/01/09)
An electrocyclic ring closure is the key step of an efficient one-pot method for the synthesis of pyrrole-2-carboxylates and -carboxamides from chalcones and glycine esters or amides. The 3,4-dihydro-2H-pyrrole intermediates generated in situ are oxidized
Synthesis of multi-substituted pyrroles using enamides and alkynes catalyzed by Pd(OAc)2 with molecular oxygen as an oxidant
Xu, Yun-He,He, Tao,Zhang, Qiu-Chi,Loh, Teck-Peng
supporting information, p. 2784 - 2786 (2014/03/21)
A cyclization reaction between enamides and alkynes catalyzed by palladium(ii) acetate is described. In this method, the molecular oxygen serves as an efficient oxidant for the Pd(ii)/Pd(0) catalytic cycle. The simple reaction conditions permit this methodology to be used as a general tool for the preparation of multi-substituted pyrroles.
A solvent-free synthesis of ethyl 3,5-diaryl-1H-pyrrole-2-carboxylates via triethylphosphite mediated reductive cyclization of ethyl 2-nitro-5-oxo-3,5- diarylpentanoates under microwave irradiation
Khajuria, Rajni,Saini, Yeshwinder,Kapoor, Kamal K.
, p. 5699 - 5702 (2013/09/24)
Ethyl 3,5-diaryl-1H-pyrrole-2-carboxylates have been synthesized in good yields from ethyl 2-nitro-5-oxo-3,5-diarylpentanoates by treatment with triethylphosphite under microwave irradiation. The integrity of the mechanism proposed has been augmented by
ORGANIC METAL COMPLEXES FOR USE IN OPTOELECTRONIC DEVICES
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, (2010/07/04)
The invention provides an organic metal complex represented by the formula (I), wherein M is a metal selected from Rh, Ir, or Pt; Y represents N or O; R1 represents a hydrogen, a halogen, a nitro group, an amino group, a hydroxyl group, a C3-C40 aromatic radical, a C1-C50 aliphatic radical, and a C3-C50 cycloaliphatic radical; R2 represents a hydrogen, C3-C20 aromatic radical, C1-C50 aliphatic radical, or a C3-C50 cycloaliphatic radical; or R1 and R2, together with the adjacent Y, may form a ring, preferably a 5- or 6-membered ring; n1 has a value of from 0 to 3; and n2 has a value of 0 to 2; m1 has a value of at least 1; and m2 has a value of at least 1 provided that m1+m2 is 3.
A study of the effects of subunit pre-orientation for diarylpyrrole esters; design of new aryl-heteroaryl fluorescent sensors
Killoran, John,Gallagher, John F.,Murphy, Paul V.,O'Shea, Donal F.
, p. 1258 - 1265 (2007/10/03)
The synthesis, single crystal X-ray structures, spectroscopic properties and molecular mechanics calculations of three systematically substituted 3,5-diaryl-1H-pyrrole-2-carboxylic acid ethyl esters 1a-c are described. The goal is to develop design princi
