Facile one-pot synthesis of cyclic N-sulfonylamidines from lactam and sulfonamide

Article abstract of DOI:10.3987/COM-15-13307

A simple method has been developed for one-pot synthesis of five-, six- And seven-membered cyclic N-sulfonylamidines from lactams and sulfonamides under mild conditions. The method involves a Vilsmeier like reaction promoted by phosphoryl chloride. Detail

Full text of DOI:10.3987/COM-15-13307

Supporting Information
FACILE ONE-POT SYNTHESIS OF CYCLIC N-SULFONYLAMIDINES FROM
LACTAM AND SULFONAMIDE
Ayinigeer Mulati and Abudureheman Wusiman*
School of Chemistry and Chemical Engineering, Xinjiang Normal University, Urumqi
830054, People’s Republic of China. E-mail: arahman@xjnu.edu.cn
Table of Contents
S2–17 1H and 13C NMR Spectra of Compounds 3a-3p
S18 Table 1. Crystal data and structure refinement details of compound 3c
S1

1H NMR spectrum (CDCl3, 400 MHz) of 3a
13C NMR spectrum (CDCl3, 100 MHz) of 3a
S2

1H NMR spectrum (CDCl3, 400 MHz) of 3b
13C NMR spectrum (CDCl3, 100 MHz) of 3b
S3

1H NMR spectrum (CDCl3, 400 MHz) of 3c
13C NMR spectrum (CDCl3, 100 MHz) of 3c
S4

1H NMR spectrum (CDCl3, 400 MHz) of 3d
13C NMR spectrum (CDCl3, 100 MHz) of 3d
S5

1H NMR spectrum (DMSO-d6, 400 MHz) of 3e
13C NMR spectrum ((DMSO-d6, 100 MHz) of 3e
S6

1H NMR spectrum (CDCl3, 400 MHz) of 3f
13C NMR spectrum (CDCl3, 100 MHz) of 3f
S7

1H NMR spectrum (CDCl3, 400 MHz) of 3g
13C NMR spectrum (CDCl3, 100 MHz) of 3g
S8

1H NMR spectrum (CDCl3, 400 MHz) of 3h
13C NMR spectrum (CDCl3, 100 MHz) of 3h
S9

1H NMR spectrum (CDCl3, 400 MHz) of 3i
13C NMR spectrum (CDCl3, 100 MHz) of 3i
S10

1H NMR spectrum (CDCl3, 400 MHz) of 3j
13C NMR spectrum (CDCl3, 100 MHz) of 3j
S11

1H NMR spectrum (CDCl3, 400 MHz) of 3k
13C NMR spectrum (CDCl3, 100 MHz) of 3k
S12

1H NMR spectrum (CDCl3, 400 MHz) of 3l
13C NMR spectrum (CDCl3, 100 MHz) of 3l
S13

1H NMR spectrum (CDCl3, 400 MHz) of 3m
13C NMR spectrum (CDCl3, 100 MHz) of 3m
S14

1H NMR spectrum (CDCl3, 400 MHz) of 3n
13C NMR spectrum (CDCl3, 100 MHz) of 3n
S15

1H NMR spectrum (CDCl3, 400 MHz) of 3o
13C NMR spectrum (CDCl3, 100 MHz) of 3o
S16

1H NMR spectrum (CDCl3, 400 MHz) of 3p
13C NMR spectrum (CDCl3, 100 MHz) of 3p
S17

Table 1. Crystal data and structure refinement details of compound 3c
Identification code
Empirical formula
Formula weight
3c
C11 H14 N2 O3 S
254.30
Temperature
296(2) K
Wavelength
0.71073 Å
Triclinic, P -1
a = 6.533(2) Å
b = 7.642(3) Å
c = 12.602(4) Å
577.6(3) A3
2, 1.462 Mg/m3
0.278 mm-1
268
Crystal system, space group
α= 105.979(4)o
β= 99.614(4) o
γ= 100.948(4) o
Unit cell dimensions
Volume
Z, Calculated density
Absorption coefficient
F(000)
Crystal size
0.35 x 0.31 x 0.25 mm
2.84 to 27.49 o
Theta range for data collection
Limiting indices
-8<=h<=8, -6<=k<=9, -16<=l<=16
3533 / 2549 [R(int) = 0.0156]
96.2 %
Reflections collected / unique
Completeness to theta = 27.49
Max. and min. transmission
Refinement method
0.9337 and 0.9089
Full-matrix least-squares on F2
Data / restraints / parameters
Goodness-of-fit on F^2
Final R indices [I>2sigma(I)]
R indices (all data)
2549 / 0 / 156
1.075
R1 = 0.0377, wR2 = 0.1057
R1 = 0.0419, wR2 = 0.1108
0.241 and -0.391 e. Å-3
Largest diff. peak and hole
S18