title: New Convenient Strategy for Annulation of Pyrimidines to Thiophenes or Furans via the One-pot Multistep Cascade Reaction of 1H-Tetrazoles with Aliphatic Amines.
abstract: A versatile, convenient, efficient and high-yield synthetic method for 2-R(3),R(4)-amino-5-R(1)-6-R(2)-thieno[2,3-d]pyrimidin-4(3H)-ones, 2-R(3),R(4)-amino-5-R(1)-6-R(2)-thieno[3,2-d]pyrimidin-4(3H)-ones, and benzofuro[3,2-d]pyrimidin-4(3H)-ones preparation has been developed. The reaction proceeded without using solvents and included several steps. A variety of thieno[2,3-d]pyrimidine and thieno[3,2-d]pyrimidine derivatives with substituents of different nature were obtained in high yields from substituted alkyl 2-(1H-tetrazol-1-yl)thiophene-3-carboxylates, 3-(1H-tetrazol-1-yl)thiophene-2-carboxylates, and 3-(1H-tetrazol-1-yl)benzofuran-2-carboxylate after their treatment with aliphatic amines.
authors.affiliation: Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine.
authors.forename: Nazariy T
authors.initials: NT
authors.lastname: Pokhodylo
authors.affiliation: Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine.
authors.forename: Olga Ya
authors.initials: OY
authors.lastname: Shyyka
authors.affiliation: Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine.
authors.forename: Vasyl S
authors.initials: VS
authors.lastname: Matiychuk
authors.affiliation: Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine.
authors.forename: Mykola D
authors.initials: MD
authors.lastname: Obushak
mesh_terms: D000588:Amines / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011743:Pyrimidines / Q000737:chemistry*; D013777:Tetrazoles / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D005663:Furans; D011743:Pyrimidines; D013777:Tetrazoles; D013876:Thiophenes
keywords: benzofuro[3,2-d]pyrimidin-4(3H)-one; heterocyclization; tetrazole; thieno[2,3-d]pyrimidin-4(3H)-one; thieno[3,2-d]pyrimidin-4(3H)-one