1219010-17-9

Basic information

• Product Name: N-(but-3-en-1-yl)-N-cyanobenzamide
• Synonyms: N-(but-3-en-1-yl)-N-cyanobenzamide
• CAS NO: 1219010-17-9
• Molecular Weight: 200.24
• Mol File: 1219010-17-9.mol

Chemical Properties

• CAS DataBase Reference: N-(but-3-en-1-yl)-N-cyanobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(but-3-en-1-yl)-N-cyanobenzamide(1219010-17-9)
• EPA Substance Registry System: N-(but-3-en-1-yl)-N-cyanobenzamide(1219010-17-9)

Safety Data

• Hazardous Substances Data: 1219010-17-9(Hazardous Substances Data)

Upstream product

• 32847-45-3 N-(but-3-en-1-yl)cyanamide 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 506-68-3 bromocyane 
• 17150-61-7 N-(but-3-en-1-yl)benzamide 
• 1219010-16-8 C₁₂H₁₁IN₂O 

Relevant articles and documents

Hydrogen Atom Transfer-Mediated Domino Cyclisation Reaction to Access (Spiro)Quinazolinones

A radical domino cyclisation reaction of N-cyanamide alkenes, mediated by hydrogen atom transfer (HAT) has been developed. This method, using PhSiH3 and catalytic Fe(acac)3, allows for the synthesis of challenging (spiro)quinazolinone scaffolds from simple, tractable (hetero)aryl carboxylic acid and cyanamide building blocks.

A Photosensitizer-Free Radical Cascade for Synthesizing CF3-Containing Polycyclic Quinazolinones with Visible Light

Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of N-cyanamide alkenes for the synthesis of functionalized quinazolinones. Importantly, the reaction is carried out under mild conditions without any addi

Visible-Light Photoredox Catalyzed Oxidative/Reductive Cyclization Reaction of N-Cyanamide Alkenes for the Synthesis of Sulfonated Quinazolinones

An efficient photocatalytic oxidative/reductive cyclization reaction of N-cyanamide alkenes with arylsulfinic acids or arylsulfonyl chlorides, which proceeds through C-S, C-C, and C-N bond formations, is reported. This photocatalytic reaction was carried out under mild conditions, which provides a new strategy for the synthesis of sulfonated quinazolinones. Furthermore, a one-pot procedure to achieve terminal alkenes has been explored via elimination of the obtained sulfonated quinazolinones under basic conditions.

Copper-Catalyzed Divergent Trifluoromethylation/Cyclization of Unactivated Alkenes

Most of the precedent copper-catalyzed trifluoromethylation reactions of unactivated alkenes concern terminal alkenes, and these processes are terminated in elimination, or nucleophilic addition, or semipinacol rearrangement, or C-H bond functionalization steps. In this study, we develop a trifluoromethylation method for both unactivated terminal and internal alkenes to enable divergent late-stage radical cyclization and achieve high molecular complexity. These cyclizations are well consistent with Baldwin's rule. Furthermore, a kinetic isotope effect (KIE) study and control reactions were conducted, and a plausible mechanism is proposed.

Radical migration of substituents of aryl groups on quinazolinones derived from N-Acyl cyanamides

A newly designed radical cascade involving N-acyl cyanamides is reported. It builds on aromatic homolytic substitutions as intermediate events and leads to complex heteroaromatic structures via an unprecedented radical migration of a substituent on aryl groups of quinazolinones (hydrogen or alkyl). Mechanistic considerations are detailed, which allowed us to devise fine control over the domino processes. The latter could be predictably stopped at several stages, depending on the reaction conditions. Finally, a surgical introduction of a trifluoromethyl substituent on a quinazolinone was achieved via the reported migration.