Diastereoselective, Multicomponent Synthesis of Pyrrolopyrazinoquinazolinones via a Tandem Quinazolinone Rearrangement/Intramolecular Ring Closure of Tautomeric (Z)-Benzamidines | Zendy

Victor A. Jaffett | Zendy; Jhewelle N. Fitz-Henley | Zendy; Muhammad M. Khalifa | Zendy; Ilia A. Guzei | Zendy; Jennifer E. Golden | Zendy

Open Access

Diastereoselective, Multicomponent Synthesis of Pyrrolopyrazinoquinazolinones via a Tandem Quinazolinone Rearrangement/Intramolecular Ring Closure of Tautomeric (Z)-Benzamidines

Author(s) -

Victor A. Jaffett,

Jhewelle N. Fitz-Henley,

Muhammad M. Khalifa,

Ilia A. Guzei,

Jennifer E. Golden

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c01955

Subject(s) - chemistry , diastereomer , quinazolinone , tautomer , intramolecular force , enantiopure drug , domino , tandem , yield (engineering) , stereochemistry , derivative (finance) , ring (chemistry) , organic chemistry , enantioselective synthesis , financial economics , metallurgy , catalysis , materials science , economics , composite material

An expedient route to enantiopure, diastereomeric pyrrolopyrazinoquinazolinones was developed following the discovery of a domino quinazolinone rearrangement-intramolecular cyclization of N-H benzamidines. A Ugi-Mumm-Staudinger sequence employing an optically pure proline derivative gave quinazolinones that, upon N -Boc deprotection, rearranged to tautomeric Z -benzamidines. Subsequent spontaneous cyclization afforded 15 diastereomeric pyrazinoquinazolinone pairs in up to 83% overall yield and 89:11 d.r which were separated easily via routine chromatographic purification-the only one required in the entire process.

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