N-Alkoxymethylation of heterocyclic compounds with diethyl phosphite via cleavage of P–O bond

• Published in: Tetrahedron Vol. 67; no. 13; pp. 2462 - 2467
• Main Authors: Quan, Zheng-Jun, Ren, Rong-Guo, Jia, Xiao-Dong, Da, Yu-Xia, Zhang, Zhang, Wang, Xi-Cun
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.04.2011; Elsevier
• Subjects: Bonding; Chemistry; Chemistry, Organic; Cleavage; Diethyl phosphite; Ethanol; Ethyl alcohol; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Inorganic salts; Kinetics and mechanisms; N-Alkylation; N3-Substituted dihydropyrimidinones; Organic chemistry; Physical Sciences; Preparations and properties; P–O cleavage; Reactivity and mechanisms; Science & Technology; Tetrahedrons; GIDSJYAVUXNYDJ-UHFFFAOYSA-N; N-Alkylation; SXWPJKGXMOJYOP-UHFFFAOYSA-N; YNUSNAMYYOEJON-UHFFFAOYSA-N; WOFYKUQBJSSXNP-UHFFFAOYSA-N; DRQQEKOMTUWUOT-UHFFFAOYSA-N; P–O cleavage; TUOSAVVUMNXEOZ-UHFFFAOYSA-N; MTIWEZWOLZINJW-UHFFFAOYSA-N; FEXSMYHVMRFNJF-UHFFFAOYSA-N; BCLCTNFGMGONNN-UHFFFAOYSA-N; VFILUPWGBQBLTG-UHFFFAOYSA-N; YJBCMGOBQZRKEP-UHFFFAOYSA-N; BBHQISMLUGXQOW-UHFFFAOYSA-N; QFVKMKADINJBDL-UHFFFAOYSA-N; MNSGOOCAMMSKGI-UHFFFAOYSA-N; Diethyl phosphite; N3-Substituted dihydropyrimidinones; AVKMPYLSTJCGML-UHFFFAOYSA-N; VAJJXKGFPILYBO-UHFFFAOYSA-N; BECSINOJAUIXPT-UHFFFAOYSA-N; XUWMZOOSKGGZNW-UHFFFAOYSA-N; LGIKGKXCBQZOLN-UHFFFAOYSA-N; BINOL; P O cleavage; BIGINELLI-TYPE; ALPHA-AMINO; ENANTIOSELECTIVE SYNTHESIS; ACIDS; EFFICIENT SYNTHESIS; ALDEHYDES; ASYMMETRIC HYDROPHOSPHONYLATION; MICHAEL ADDITION; PHOSPHONATES; Ethanol; Nitrogen heterocycle; Alkoxycarbonylation; Pyrimidone derivatives; Alkylation; Azides; P―O cleavage; Reaction mechanism; Cleavage; Chemical synthesis
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.01.061

N-Alkoxymethylation of heterocyclic compounds with diethyl phosphite via cleavage of P–O bond was investigated and a series of N3-ethoxymethylated heterocyclic compounds were synthesized. A mechanism in which diethyl phosphite acts as an efficient surrogate of ethanol was proposed and supported by several evidences. [Display omitted]