Saturated heterocycles, 75. Preparation of tetracyclic thiophene derivatives with bridgehead nitrogen. Synthesis of polymethylenethieno[2,3-d]dihydropyrrolo-, tetrahydropyrido- and tetrahydroazepino[1,2-a]pyrimidin-4-ones and -4-thiones

Katalin Csukonyi, János Lázár, G. Bernáth, I. Hermecz, Zoltán Mészáros

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The following tetracyclic ring systems and their derivatives have been synthesized for pharmacological investigations: Trimethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and -4-thione (1 a, 5 a); Tetramethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and -4-thione (1 b, 1 j, 5 b); Pentamethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and-4-thione (1 c, 5 c); Trimethylenethieno[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one and -4-thione (1 d, 5 d); Tetramethylenethieno[2,3-d]tetrahydropyrido[1,2,-a]pyrimidin-4-one and -4-thione (1 e, 5 e); Pentamethylenethieno[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one and -4-thione (1 f, 5 f); Trimethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one and -4-thione (1 g, 5 g); Tetramethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-on and -4-thione (1 h, 5 h); Pentamethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one and -4-thione (1 i, 5 i); Tentamethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one (7 b); Pentamethylenethieno-[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one (7 c). Compounds 1 a-i were synthesized from 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene 2 a-c with the corresponding lactim ethers (3 a-c) in chlorobenzene in the presence of polyphosphoric acid (PPA). Compounds 7 b and 7 c were obtained in the reaction of β-amino acid esters 2 b and 2 c with 2-bromopyridine (6). The thione derivatives (5 a-i) were prepared from compounds 1 a-i with phosphorus(V) sulphide.

Original languageEnglish
Pages (from-to)1295-1303
Number of pages9
JournalMonatshefte fur Chemie
Volume117
Issue number11
DOIs
Publication statusPublished - Nov 1986

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Thiones
Thiophenes
Nitrogen
Derivatives
Ethers
Sulfides
Phosphorus
Esters

Keywords

  • Condensation of 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene with lactim ethers and 2-bromopyridine
  • Oxo-thio exchange

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

@article{251b78352078495f973d318e7fe7c374,
title = "Saturated heterocycles, 75. Preparation of tetracyclic thiophene derivatives with bridgehead nitrogen. Synthesis of polymethylenethieno[2,3-d]dihydropyrrolo-, tetrahydropyrido- and tetrahydroazepino[1,2-a]pyrimidin-4-ones and -4-thiones",
abstract = "The following tetracyclic ring systems and their derivatives have been synthesized for pharmacological investigations: Trimethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and -4-thione (1 a, 5 a); Tetramethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and -4-thione (1 b, 1 j, 5 b); Pentamethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and-4-thione (1 c, 5 c); Trimethylenethieno[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one and -4-thione (1 d, 5 d); Tetramethylenethieno[2,3-d]tetrahydropyrido[1,2,-a]pyrimidin-4-one and -4-thione (1 e, 5 e); Pentamethylenethieno[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one and -4-thione (1 f, 5 f); Trimethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one and -4-thione (1 g, 5 g); Tetramethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-on and -4-thione (1 h, 5 h); Pentamethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one and -4-thione (1 i, 5 i); Tentamethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one (7 b); Pentamethylenethieno-[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one (7 c). Compounds 1 a-i were synthesized from 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene 2 a-c with the corresponding lactim ethers (3 a-c) in chlorobenzene in the presence of polyphosphoric acid (PPA). Compounds 7 b and 7 c were obtained in the reaction of β-amino acid esters 2 b and 2 c with 2-bromopyridine (6). The thione derivatives (5 a-i) were prepared from compounds 1 a-i with phosphorus(V) sulphide.",
keywords = "Condensation of 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene with lactim ethers and 2-bromopyridine, Oxo-thio exchange",
author = "Katalin Csukonyi and J{\'a}nos L{\'a}z{\'a}r and G. Bern{\'a}th and I. Hermecz and Zolt{\'a}n M{\'e}sz{\'a}ros",
year = "1986",
month = "11",
doi = "10.1007/BF00810875",
language = "English",
volume = "117",
pages = "1295--1303",
journal = "Monatshefte fur Chemie",
issn = "0026-9247",
publisher = "Springer Wien",
number = "11",

}

TY - JOUR

T1 - Saturated heterocycles, 75. Preparation of tetracyclic thiophene derivatives with bridgehead nitrogen. Synthesis of polymethylenethieno[2,3-d]dihydropyrrolo-, tetrahydropyrido- and tetrahydroazepino[1,2-a]pyrimidin-4-ones and -4-thiones

AU - Csukonyi, Katalin

AU - Lázár, János

AU - Bernáth, G.

AU - Hermecz, I.

AU - Mészáros, Zoltán

PY - 1986/11

Y1 - 1986/11

N2 - The following tetracyclic ring systems and their derivatives have been synthesized for pharmacological investigations: Trimethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and -4-thione (1 a, 5 a); Tetramethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and -4-thione (1 b, 1 j, 5 b); Pentamethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and-4-thione (1 c, 5 c); Trimethylenethieno[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one and -4-thione (1 d, 5 d); Tetramethylenethieno[2,3-d]tetrahydropyrido[1,2,-a]pyrimidin-4-one and -4-thione (1 e, 5 e); Pentamethylenethieno[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one and -4-thione (1 f, 5 f); Trimethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one and -4-thione (1 g, 5 g); Tetramethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-on and -4-thione (1 h, 5 h); Pentamethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one and -4-thione (1 i, 5 i); Tentamethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one (7 b); Pentamethylenethieno-[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one (7 c). Compounds 1 a-i were synthesized from 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene 2 a-c with the corresponding lactim ethers (3 a-c) in chlorobenzene in the presence of polyphosphoric acid (PPA). Compounds 7 b and 7 c were obtained in the reaction of β-amino acid esters 2 b and 2 c with 2-bromopyridine (6). The thione derivatives (5 a-i) were prepared from compounds 1 a-i with phosphorus(V) sulphide.

AB - The following tetracyclic ring systems and their derivatives have been synthesized for pharmacological investigations: Trimethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and -4-thione (1 a, 5 a); Tetramethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and -4-thione (1 b, 1 j, 5 b); Pentamethylenethieno[2,3-d]dihydropyrrolo[1,2-a]pyrimidin-4-one and-4-thione (1 c, 5 c); Trimethylenethieno[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one and -4-thione (1 d, 5 d); Tetramethylenethieno[2,3-d]tetrahydropyrido[1,2,-a]pyrimidin-4-one and -4-thione (1 e, 5 e); Pentamethylenethieno[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one and -4-thione (1 f, 5 f); Trimethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one and -4-thione (1 g, 5 g); Tetramethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-on and -4-thione (1 h, 5 h); Pentamethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one and -4-thione (1 i, 5 i); Tentamethylenethieno[2,3-d]tetrahydroazepino[1,2-a]pyrimidin-4-one (7 b); Pentamethylenethieno-[2,3-d]tetrahydropyrido[1,2-a]pyrimidin-4-one (7 c). Compounds 1 a-i were synthesized from 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene 2 a-c with the corresponding lactim ethers (3 a-c) in chlorobenzene in the presence of polyphosphoric acid (PPA). Compounds 7 b and 7 c were obtained in the reaction of β-amino acid esters 2 b and 2 c with 2-bromopyridine (6). The thione derivatives (5 a-i) were prepared from compounds 1 a-i with phosphorus(V) sulphide.

KW - Condensation of 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene with lactim ethers and 2-bromopyridine

KW - Oxo-thio exchange

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