Facile solid phase synthesis of 1,2-disubstituted-6-nitro-1,4- dihydroquinazolines using a tetrafunctional scaffold

Xiaobing Wang, Aimin Song, Seth Dixon, Mark J. Kurth, Kit Lam

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Solid phase synthesis of 1, 2-disubstituted-6-nitro-1,4-dihydroquinazolines is described. The new tetrafunctional scaffold N-Alloc-3-amino-3-(2-fluoro-5- nitrophenyl)propionic acid was prepared by nitration of 3-amino-3-(2- fluorophenyl)propionic acid. The scaffold was anchored to Rink resin via its carboxylic group and treated with primary amines to displace the arylfluorine followed by cyclization with aryl isothiocyanates in the presence of DIC upon Alloc deprotection to afford 1,2-disubstituted-6-nitro-1,4-dihydroquinazolines in high yield.

Original languageEnglish (US)
Pages (from-to)427-430
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number3
DOIs
StatePublished - Jan 17 2005

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Solid-Phase Synthesis Techniques
Scaffolds
Isothiocyanates
Nitration
Dacarbazine
Cyclization
Amines
Resins
propionic acid

Keywords

  • Quinazoline
  • Solid phase synthesis
  • Tetrafunctional scaffold

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Facile solid phase synthesis of 1,2-disubstituted-6-nitro-1,4- dihydroquinazolines using a tetrafunctional scaffold. / Wang, Xiaobing; Song, Aimin; Dixon, Seth; Kurth, Mark J.; Lam, Kit.

In: Tetrahedron Letters, Vol. 46, No. 3, 17.01.2005, p. 427-430.

Research output: Contribution to journalArticle

Wang, Xiaobing ; Song, Aimin ; Dixon, Seth ; Kurth, Mark J. ; Lam, Kit. / Facile solid phase synthesis of 1,2-disubstituted-6-nitro-1,4- dihydroquinazolines using a tetrafunctional scaffold. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 3. pp. 427-430.
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AB - Solid phase synthesis of 1, 2-disubstituted-6-nitro-1,4-dihydroquinazolines is described. The new tetrafunctional scaffold N-Alloc-3-amino-3-(2-fluoro-5- nitrophenyl)propionic acid was prepared by nitration of 3-amino-3-(2- fluorophenyl)propionic acid. The scaffold was anchored to Rink resin via its carboxylic group and treated with primary amines to displace the arylfluorine followed by cyclization with aryl isothiocyanates in the presence of DIC upon Alloc deprotection to afford 1,2-disubstituted-6-nitro-1,4-dihydroquinazolines in high yield.

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