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Regioselective synthesis of fused imidazo[1,2-a]pyrimidines via intramolecular C-N bond formation/6-endo-dig cycloisomerization.
J Org Chem. 2014 Aug 01; 79(15):6905-12.JO

Abstract

An efficient regioselective cascade synthesis of N-fused imidazo heterocycles has been developed. This cascade transformation proceeds via a transition-metal (copper/silver) catalyzed coupling reaction between 2-aminobenzimidazole, aldehydes, and alkynes leading to the formation of propargylamine intermediate, which regioselectively undergoes 6-endo-dig cyclization through intramolecular N-H bond activation interceded C-N bond formation leading to highly functionalized imidazo[1,2-a]pyrimidines in good to excellent yields.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kumar A
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute , Sector 10, Jankipuram Extension, Lucknow 226031 India.
Kumar M
No affiliation info available
Maurya S
No affiliation info available
Khanna RS
No affiliation info available

MeSH

AldehydesBenzimidazolesCatalysisCyclizationHeterocyclic CompoundsMolecular StructurePyrimidinesStereoisomerismTransition Elements

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24988318

Citation

Kumar, Atul, et al. "Regioselective Synthesis of Fused Imidazo[1,2-a]pyrimidines Via Intramolecular C-N Bond Formation/6-endo-dig Cycloisomerization." The Journal of Organic Chemistry, vol. 79, no. 15, 2014, pp. 6905-12.
Kumar A, Kumar M, Maurya S, et al. Regioselective synthesis of fused imidazo[1,2-a]pyrimidines via intramolecular C-N bond formation/6-endo-dig cycloisomerization. J Org Chem. 2014;79(15):6905-12.
Kumar, A., Kumar, M., Maurya, S., & Khanna, R. S. (2014). Regioselective synthesis of fused imidazo[1,2-a]pyrimidines via intramolecular C-N bond formation/6-endo-dig cycloisomerization. The Journal of Organic Chemistry, 79(15), 6905-12. https://doi.org/10.1021/jo5007762
Kumar A, et al. Regioselective Synthesis of Fused Imidazo[1,2-a]pyrimidines Via Intramolecular C-N Bond Formation/6-endo-dig Cycloisomerization. J Org Chem. 2014 Aug 1;79(15):6905-12. PubMed PMID: 24988318.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regioselective synthesis of fused imidazo[1,2-a]pyrimidines via intramolecular C-N bond formation/6-endo-dig cycloisomerization. AU - Kumar,Atul, AU - Kumar,Mukesh, AU - Maurya,Shivam, AU - Khanna,Ranjana S, Y1 - 2014/07/14/ PY - 2014/7/3/entrez PY - 2014/7/6/pubmed PY - 2015/2/13/medline SP - 6905 EP - 12 JF - The Journal of organic chemistry JO - J Org Chem VL - 79 IS - 15 N2 - An efficient regioselective cascade synthesis of N-fused imidazo heterocycles has been developed. This cascade transformation proceeds via a transition-metal (copper/silver) catalyzed coupling reaction between 2-aminobenzimidazole, aldehydes, and alkynes leading to the formation of propargylamine intermediate, which regioselectively undergoes 6-endo-dig cyclization through intramolecular N-H bond activation interceded C-N bond formation leading to highly functionalized imidazo[1,2-a]pyrimidines in good to excellent yields. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/24988318/Regioselective_synthesis_of_fused_imidazo[12_a]pyrimidines_via_intramolecular_C_N_bond_formation/6_endo_dig_cycloisomerization_ DB - PRIME DP - Unbound Medicine ER -